Substituted pyrimidines, processes for their preparation, and their use as pesticides and fungicides

ABSTRACT

Substituted 4-amino- and 4-alkoxy-cycloalkylpyrimidines, processes for their preparation, and their use as pesticides and fungicides 
     The invention relates to compounds of the formula                    
     in which R 1 , R 2 , R 3  and Q are as defined in the description, X is NH or oxygen and E is a bond or a 1- to 4-membered carbon chain, to a process for their preparation, to agents containing them, and to their use in the control of pests and as fungicides.

This application is a division of application Ser. No. 08/029,889, filedMar. 11, 1993 now U.S. Pat. No. 5,571,815.

The invention relates to novel substituted 4-amino- and4-alkoxypyrimidines, to processes for their preparation and to their useas pesticides, in particular as insecticides, acaricides and fungicides.

It has already been disclosed that certain substituted4-aminopyrimidines have a good fungicidal, acaricidal and insecticidalactivity (cf. EP-A-57,440, EP-A-196,524, EP-A-264,217, EP-A-276,406,EP-A-323,757, EP-A-326,328, EP-A-326,329, EP-A-326,330, EP-A-356,158,EP-A-370,704, EP-A-411,634, EP-A-424,125, EP-A-452,002, EP-A-459,611,EP-A-447,891). However, the biological activity of these compounds isnot satisfactory in all fields of application, in particular when lowdosage rates and concentrations are used.

Novel substituted 4-amino- and 4-alkoxypyrimidines of the formula I havebeen found,

in which

R¹ is hydrogen, halogen, (C₁-C₄)-alkyl or (C₃-C₆)-cycloalkyl,

R² is hydrogen, (C₁-C₄)-alkyl, halogen (C₁-C₄)-halo-alkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-alkylaminoor di-(C₁-C₄)-alkylamino,

R³ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,halogen, (C₁-C₄)-alkylthio, amino, (C₁-C₄)-alkylamino ordi-(C₁-C₄)-alkylamino or

R² and R³ together with the carbon atoms to which they are bonded forman unsaturated 5- or 6-membered isocyclic ring which, if it is a5-membered ring, can contain an oxygen or sulfur atom in place of CH₂and which is optionally substituted by 1, 2 or 3 identical or differentradicals, these radicals being (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-halo-alkyl, preferably trifluoromethyl, (C₁-C₄)-halo-alkoxyand/or halogen, or

R² and R³ together with the carbon atoms to which they are bonded form asaturated 5-, 6- or 7-membered isocyclic ring which can contain anoxygen or sulfur atom in place of CH₂ and which is optionallysubstituted by 1, 2 or 3 (C₁-C₄)-alkyl groups,

X is NH or oxygen,

E is a direct bond or a straight-chain or branched (C₁-C₄)-alkanediylgroup, preferably a direct bond,

Q has the meaning Q¹ and

Q¹ is a cycloalkyl group of the formula II

 in which n is an integer from 2 to 7,

R⁴ and R⁵ are identical or different and are in each case hydrogen,(C₁-C₁₂)-alkyl, (C₃-C₈)-cycloalkyl, (C₃-C₈)-cyclo alkyl-(C₁-C₄)-alkyl,(C₁-C₈)-alkoxy, (C₃-C₈)-cyclo-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₃-C₈)-cyclo-alkyl-(C₁-C₄)-alkoxy, tri-(C₁-C₈)-alkylsilyl, preferablydimethyl-(C₁-C₈)-alkylsilyl or tri-ehtylsilyl,di-(C₁-C₈)-alkyl-(C₃-C₈)-cycloalkyl-silyl, preferablydimethylcyclohexylsilyl, di-(C₁-C₈)-alkyl (phenyl-(C₁-C₄)-alkyl)-silyl,preferably dimethyl-(phenyl-(C₁-C₄)-alkyl)silyl,di-(C₁-C₈)-alkyl-(C₁-C₄)-haloalkylsilyl, preferablydimethyl-(C₁-C₄)-haloalkylsilyl, dimethylphenyl-silyl,(C₁-C₄)-haloalkyl, halogen, (C₁-C₄)-haloalkoxy, heteroaryl, phenyl,phenyl-(C₁-C₄)-alkyl, benzyloxy, benxzyloxy-(C₁-C₄)-alkyl, benzylthio,phenylthio or phenoxy, it being possible for the phenyl rings in theseven last-mentioned radicals to be unsubstituted or provided with oneor two substituents and these substituents are identical or differentand can be in each case (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl,(C₁-C₄)-haloalkyl, preferably trifluoromethyl, halogen,(C₁-C₄)-dialkylamino, (C₁-C₄)-alkylthio, (C₁-C₈)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,H₅C₂-O-[CH₂-CH₂-O-]_(x), 2-(tetrahydro-2H-pyran-2-yloxy)-ethoxy,(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, benzyloxy which in the phenyl radicaloptionally carries one or two identical or different substituentsselected from the group comprising (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and halogen, ortri-(C₁-C₄)-alkylsilylmethoxy, preferablydimethyl-(C₁-C₄)-alkylsilylmethoxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy,1,3-dioxolan-2-ylmethoxy, tetrahydro-furan-2-ylmethoxy ortetrahydro-2H-pyran-2-ylmethoxy, where, both, R⁴ and R⁵ do notcoincidentally denote hydrogen, and where, in two adjacent substituentswhich are identical or different and are selected from the groupcomprising (C₁-C₈)-alkyl and (C₁-C₈)-alkoxy, in each case one hydrogenatom can be replaced by a joint carbon-carbon bond which links these twosubstituents, or

R⁴ and R⁵ together with the cycloalkyl group form a 3-8-memberedspirocyclic, preferably saturated spirocyclic, ring system which cancontain oxygen or sulfur in place of one or two CH₂ groups or

R⁴ and R⁵ together with the carbon atoms carrying them form a fused 5-or 6-membered, preferably saturated isocycle, in particular acyclopentane or cyclohexane system,

X is 2, 3 or 4, preferably 2, or

Q has the meaning Q² and

Q² is a group of the formula III

in which

R⁶ is a group of the formula Z-W and Z is a direct bond or carbonyl orsulfonyl and W is an aryl or heteroaryl group which can be unsubstitutedor provided with one or two substituents and these substituents areidentical or different and are in each case (C₁-C₈)-alkyl,(C₃-C₈)-cycloalkyl, trifluoromethyl, halogen (C₁-C₄)-alkoxy,(C₁-C₄)-dialkylamino or (C₁-C₄)-alkylthio.

If Q has the meaning Q¹, R² and R³ together with the carbon atomscarrying them form an unsaturated 6-membered isocyclic ring and R⁴ andR⁵ form a fused 5- or 6-membered ring, then the meaning 5-membered ringis preferred for the two last-mentioned radicals.

If Q has meaning Q¹, and R² and R³ together with the carbon atomscarrying them form a furan or thiophene system, then Q¹ is preferablynot (C₃-C₈)-cycloalkyl which is optionally substituted and thesubstituents are in particular alkyl such as (C₁-C₄)-alkyl, alkoxy suchas (C₁-C₄)-alkoxy, haloalkyl such as (C₁-C₄)-haloalkyl, haloalkoxy suchas (C₁-C₄)-haloalkoxy or halogen.

Preferred compounds of the formula I are those in which

R¹ is hydrogen, methyl or cyclopropyl,

R² is (C₁-C₄)-alkyl, chlorine, methoxy, ethoxy or methoxymethyl,

R³ is hydrogen, (C₁-C₃)-alkyl, methoxy, ethoxy or halogen or

R² and R³ together with the carbon atoms to which they are bonded forman unsaturated 5- or 6-membered ring which can contain an oxygen orsulfur atom, or R² and R³ together with the carbon atoms to which theyare bonded form a saturated 5- or 6-membered ring which can contain asulfur atom,

Q has the meaning Q¹ or Q², in particular those compounds of the formulaI in which

R¹ is hydrogen or methyl,

R² is methyl, ethyl, methoxy, ethoxy or methoxy-methyl,

R³ is methyl, ethyl, methoxy, chlorine or bromine, or

R² and R³ together with the carbon atoms to which they are bonded formthe quinazoline system, or

R² and R³ together with the carbon atoms to which they are bonded form asaturated 6-membered ring which can contain a sulfur atom and

Q has the meaning Q¹ or Q², preferably those compounds of the formula Iin which

E is a direct bond,

R¹ is hydrogen,

R² is methyl, ethyl or methoxymethyl,

R³ is chlorine, bromine or methoxy or

R² and R³ together with the carbon atoms to which they are bonded formthe quinazoline system which can be substituted by fluorine, chlorine,bromine or methyl, or

R² and R³ together with the pyrimidine ring form the5,6,7,8-tetrahydroquinazoline system or the5,6-dihydro-7H-thiopyrano[2,3-d]pyrimidine or the5,6-dihydro-8H-thiopyrano[3,4-d]pyrimidine system

 and

Q has the meaning Q¹ or Q².

Very particularly preferred compounds of the formula I are those inwhich

E is a direct bond,

R¹ is hydrogen,

R² is methoxymethyl and R³ is methoxy or

R² is methyl or ethyl and R³ is chlorine or bromine or

R² and R³ together with the carbon atom to which they are bonded form aquinazoline system which is substituted by fluorine, chlorine or methyl,or form a 5,6,7,8-tetrahydroquinazoline system and

Q has the meaning Q¹, in particular those compounds of the formula I inwhich

E is a direct bond,

R¹ is hydrogen,

R² is methoxymethyl and R³ is methoxy or

R² is ethyl and R³ is chlorine or

R² and R³ together with the carbon atom to which they are bonded form aquinazoline or a 5,6,7,8-tetrahydroquinazoline system and

Q is a cycloalkyl group of the formula II which is substituted in the 3-or 4-position and in which

n is 4 or 5,

R⁴ is (C₃-C₈)-alkyl, cyclopentyl, cyclohexyl, phenyl or phenoxy, itbeing possible for the two last-mentioned radicals to be unsubstitutedor provided with one or two substituents which can be identical ordifferent and which are fluorine chlorine, bromine, (C₁-C₄)-alkyl,(C₁-C₄)-alkoxy, trifluoromethyl, (C₁-C₂)-haloalkoxy, cyclohexyl,2-ethoxyethoxy, methylthio or dimethylamino, and

R⁵ is hydrogen.

Other very particularly preferred compounds of the formula I are thosein which

E is a direct bond,

R¹ is hydrogen,

R² is methoxymethyl and R³ is methoxy or

R² is ethyl and R³ is chlorine, or

R² and R³ together with the carbon atoms to which they are bonded form aquinazoline or a 5,6,7,8-tetrahydroquinazoline system,

Q has the meaning Q¹ and

Q¹ is cyclohexyl which is substituted in the 4-position, and E and thesubstituent in the 4-position of the cyclohexyl are in the cis-positionrelative to each other,

R⁴ is as defined above and

R⁵ is preferably hydrogen.

In the above formula I, “halogen” is to be understood as meaning afluorine, chlorine, bromine or iodine atom, preferably a fluorine,chorine or bromine atom, the term “(C₁-C₄)-alkyl” is to be understood asmeaning an unbranched or branched hydrocarbon radical having 1-4 carbonatoms such as, for example, the methyl, ehtyl, propyl, 1-methylethyl,1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl radical, the term“(C₁-C₈)-alkyl” is to be understood as meaning the abovementioned alkylradicals and, for example, the pentyl, 2methylbutyl or1,1-dimethylpropyl radical, the hexyl, heptyl, octyl radical, or1,1,3,3-tetramethylbutyl; the term “(C₁-C₁₂)-alkyl” is to be understoodas meaning the abovementioned alkyl radicals as well as, for example,the nonyl, decyl, undecyl or dodecyl radical; the term“(C₃-C₈)-cycloalkyl” is to be understood as meaning the cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group;the term “(C₁-C₄)-alkoxy” is to be understood as meaning an alkoxy groupwhose hydrocarbon radical has the meaning given for the term“(C₁-C₄)-alkyl”; the term “(C₃-C₈)-cycloalkoxy” is to be understood asmeaning a cycloalkoxy group whose hydrocarbon radical has the meaninggiven under “(C₃-C₈)-cycloalkyl”; the term “(C₁-C₄)-alkylthio” is to beunderstood as meaning an alkylthio group whose hydrocarbon radical hasthe meaning given for the term “(C₁-C₄)-alkyl”; the term“(C₁-C₄)-haloalkoxy” is to be understood as meaning a haloalkoxy groupwhose halohydrocarbon radical has the meaning given for the term“(C₁-C₄)-haloalkyl”, the term “(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl” is to beunderstood as meaning, for example, a 1-methoxyethyl group, a2-methoxyethyl group, a 2-ethoxyethyl group, a methoxymethyl orethoxymethyl group, a 3-methoxypropyl group or a 4-butoxybutyl group;the term “(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl” is to be understood asmeaning, for example, methylthiomethyl, ethylthiomethyl,propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or3-methylthiopropyl; the term “(C₁-C₄)-alkylamino” is to be understood asmeaning an alkylamino group whose hydrocarbon radical has the meaninggiven under the term “(C₁-C₄)-alkyl”, preferably the ethyl andmethylamino group; the term “di-(C₁-C₄)-alkylamino” is to be understoodas meaning a dialkylamino group whose hydrocarbon radicals have themeaning given under the term “(C₁-C₄)-alkyl”, preferably the dimethyland diethylamino group; the term “(C₁-C₄)-haloalkyl” is to be understoodas meaning an alkyl group mentioned under the term “(C₁-C₄)-alkyl”, inwhich one or more hydrogen atoms is replaced by the abovementionedhalogen atoms, preferably chlorine or fluorine, such as, for example,the trifluoromethyl group, the 2,2,2-trifluoroethyl group, thechloromethyl or the fluoromethyl group, the difluoro-methyl group or the1,1,2,2-tetrafluoroethyl group; the term(C₃-C₈)-cycloalkyl-(C₂-C₄)-alkyl” is to be understood as meaning one ofthe abovementioned (C₁-C₄)-alkyl groups which is substituted by one ofthe abovementioned (C₃-C₈)-cycloalkyl groups, for examplecyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, cyclohexylbutyl or1-cyclohexyl-1-methyl-ethyl; the term “phenyl-(C₁-C₄)-alkyl” is to beunderstood as meaning one of the abovementioned (C₁-C₄)-alkyl groupswhich is substituted by a phenyl group, for example the benzyl group,the 2-phenylethyl group, the 1-phenylethyl group, the1-mehtyl-1-phenylethyl group, the 3-phenylpropyl group, the4-phenylbutyl group or the 2-methyl-2-phenylethyl group; the term “aryl”is to be understood as meaning, for example, phenyl, naphthyl orbiphenylyl, preferably phenyl; the term “heteroaryl” is to be understoodas meaning an aryl radical in which at least one CH group is replaced byN and/or at least two adjacent CH groups are replaced by S, NH or O; theterm “benzyloxy-(C₁-C₄)-alkyl” is to be understood as meaning a(C₁-C₄)-alkyl group which has the abovementioned meanings and which issubstituted by a benzyloxy group, for example the benzyloxymethyl or the2-(benzyloxy)-ethyl group; the term “(C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy”is to be understood as maning a (C₁-C₄)-alkoxy group which has theabovementioned meanings and which is substituted by a (C₃-C₈)-cycloalkylgroup which has the abovementioned meanings, for example thecyclopropylmethyl or the cyclohexylmethyl group; the term“tri-(C₁-C₈)-alkylsilyl” is to be understood as meaning a trialkylsilylgroup which carries preferably two methyl groups and one (C₁-C₈)-alkylgroup having the abovementioned meanings, for example thetrimethylsilyl, the dimethylethylsilyl or the dimethyloctylsilyl group;the term “di-(C₁-C₈)-alkyl-(C₁-C₄)-haloalkylsilyl” is to be understoodas meaning a silyl radical which carries preferably two methyl groupsand one (C₁-C₄)-haloalkyl radical having the meanings given under theterm (C₁-C₄)-haloalkyl, for example thedimethyl-3,3,3-trifluoropropylsilyl radical; the term“(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy” is to be understood as meaning, forexample, the ethoxymethoxy, 2-ethoxyethoxy, 2-butoxyethoxy or2-methoxyethoxy group; the term “(C₂-C₈)-alkenyl” is to be understood asmeaning, for example, the allyl, 1-methylallyl, 2butenyl or3-methyl-2-butenyl group; the term “(C₂-C₈)-alkynyl” is to be understoodas meaning, for example, the propargyl, 2-butynyl or 2-pentynyl group;the term “tri-(C₁-C₄)-alkylsilylmethoxy” is to be understood as meaninga trialkylsilylmethoxy radical which has preferably 2 methyl groups andin which the (C₁-C₄)-alkyl group has the abovementioned meanings; andthe term “di-(C₁-C₈)-alkyl-phenyl-(C₁-C₄)-alkylsilyl” is to beunderstood as meaning a trialkylsilyl radical which has preferably twomethyl groups and in which one alkyl group has the meanings mentionedabove for the term “phenyl-(C₁-C₄)-alkyl”, preferably thedimethylbenzylsilyl group.

What has been explained above applies correspondingly to homologues orradicals derived thereof.

The present invention relates to the compounds of the formula I in theform of the free base or of an acid addition salt. Acids which can beused for salt formatoin are inorganic acids such as hydrochloric acid,hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, ororganic acids such as formic acid, acetic acid, propionic acid, malonicacid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid,methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid.

Some of the compounds of the formula I have one or more asymmetriccarbon atoms. Racemates and diastereomers can therefore occur. Theinvention embraces the pure isomers as well as their mixtures. Thediastereomer mixtures can be resolved into the components by customarymethods, for example by selective crystallization from suitable solventsor by chromatography. Racemates can be resolved to give the enantiomersby conventional methods, for example by salt formation with an opticallyactive acid, separation of the diasteromeric salts and liberation of thepure enantiomers by means of a base.

If Q¹ is a cycloalkyl group of the formula II and n is 4, 5 or 6,preferably 5, then E and a radical R⁴ or R⁵ which is preferably in the4-position if n=5 are preferably in the cis-configuration relative toeach other.

The invention furthermore relates to a process for the preparation ofcompounds of the formula I, which comprises reacting a compound of theformula IV

in which R¹, R² are as defined in formula I and Z is a leaving group,for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy,alkylsulfonyl or arylsulfonyl, with a nucleophile of the formula V

HX−E−Q  (V)

in which X, E and Q are as defined in formula I and, if R³ is hydrogen,the resulting compounds of the formula I are optionally chlorinated orbrominated on carbon atom 5 of the pyrimidine.

The above mentioned substitution reaction is known in principle. Theleaving group Z can be varied within wide limits and can be, forexample, a halogen atom such as fluorine, chlorine, bromine or iodine,or alkylthio such as methyl- or ethylthio, or alkanesulfonyloxy such asmethane-, trifluoromethane- or ethanesulfonyloxy, or arylsulfonyloxysuch as benxenesulfonyloxy or toluenesulfonyloxy, or alkylsulfonyl suchas methyl- or ethylsulfonyl, or arylsulfonyl such as phenyl- ortoluenesulfonyl.

The abovementioned reaction is carried out in a temperature range of20-150° C., expediently in the presence of a base and if appropriate inan inert organic solvent such as N,N-dimethylformamide,N,N-diemthylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one,dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol,butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene,chlorobenzene or xylene. Mixtures of the solvents mentioned can also beused.

In the event that X is oxygen, then suitable bases are, for example,carbonates, hydrogen carbonates, amides or hydrides of alkali metals oralkaline earth metals such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate, sodium amide or sodium hydride, and inthe event that X is NH, they are, for example, carbonates, hydrogencarbonates, hydroxides, amides or hydrides of alkali metals or alkalineearth metals such as sodium carbonate, sodium hydrogen carbonate,potassium carbonate, sodium hydroxide, sodium amide or sodium hydride,or organic bases such as triethylamine or pyridine. A second equivalentof an amine V can also be used as auxiliary base.

The starting compounds of the formula IV can be prepared by processeswhich are analogous to known processes. The starting materials used areacetoacetic ester derivatives which are converted into thehalopyrimidines via the corresponding hydroxypyrimidines:

Furthermore, the starting compounds of the formula IV can be obtainedfrom malonic ester derivatives in analogy to known processes:

In the event that X is oxygen, the nucleophiles of the formula V, whichare required as starting materials, can be prepared by known processes,for example by reducing a carbonyl group with a suitable reducing agent,for example a complex metal hydride or, in the case of an aldehyde orketone, also using hydrogen and a hydrogenation catalyst. Otherpossibilities are the reaction of an organometal compound with acarbonyl group or an oxirane. To synthesize cyclohexanol derivatives, itis also possible to react suitable substituted phenols with hydrogen inthe presence of a hydrogenation catalyst.

In the event that X is NH, the nucleophiles of the formula V, which arerequired as starting materials, can also be prepared by known methods,for example reduction of an oxime or of a nitrile with a suitablereducing agent, for example a complex metal hydride or hydrogen in thepresence of a hydrogenation catalyst, reductive amination orLeuckart-Wallach reaction of an aldehyde or ketone or Gabriel reactionof an alkyl halide or alkyl tosylate. To synthesize cyclohexylaminederivatives, it is also possible to react suitable substituted anilineswith hydrogen in the presence of a hydrogenation catalyst.

The compounds of the formula I in which R³ is halogen can be halogenatedby known processes.

In the case of the 5-chloro derivatives, substances which can be usedare, for example, elemental chlorine, sodium hypochlorite, sulfurylchloride or N-chlorosuccinimide, and particularly suitable for thebromination are elemental bromine or N-bromosuccinimide. Examples ofsuitable solvents are dichloromethane, chloroform or glacial aceticacid.

The active ingredients are suitable for controlling animal pests, inparticular insects, arachnids, helminths and molluscs, very particularlypreferably for controlling insects and arachnids, which can be found inagriculture, in livestock breeding, in forests, in the protection ofstored goods and materials as well as in the field of hygiene, and theyare well tolerated by plants and have a favorable toxicity towarm-blooded species. They are active against normally-sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of the Acarina, for example Acarus siro, Agras spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp,.Tarsonemus spp., Bryobia praetiosa, Panonychus spp,. Tetranychus spp.,Eotetranychus spp., Oligonychus spp., Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpohagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporisHaematopinus spp. andLinognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosomalangerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp., and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatristhruberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Cacoceia podana,Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homonamagnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp,. Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilla spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the class of the Helminthes, for example, Haemonchus,Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides,Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis aswell as Fasciola and phytopathogenic nematodes, for example those fromthe genera Meloidogyne, Heterodera, Ditylenchus, Aphelenchoides,Radopholus, Globodera, Pratylenchus, Longidorus and Xiphinema.

From the class of the Gastropoda, for example, Deroceras spp., Arionspp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp.,Bulinus spp., and Oncomelania spp.

From the class of the Bivalva, for example, Dreissena spp.

The invention also relates to insecticidal and acaricidal agents whichcontain the compounds of the formula I, besides suitable formulationauxiliaries.

The agents according to the invention generally contain the activesubstances of the formula I to the extent of 1 to 95% by weight.

They can be formulated in various ways, depending on the prevailingbiological and/or chemico-physical parameters. The following aretherefore possible for formulation: wettable powders (WP), emulsifiableconcentrates (EC), aqueous solutions (SC), emulsions, sprayablesolutions, dispersions on an oil or water basis (SC), suspoemulsions(SC), dusts (DP), seed-dressing agents, granules in the form ofmicrogranules, spray granules, coated granules and adsorption granules,water-dispersible granules (WG), ULV formulations, microcapsules, waxesor baits.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986;van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Ed.1972-73; K. Martens, “Spray Drying Handbook”, 3rd Ed. 1979, G. GoodwinLtd. London.

The formulation auxiliaries which are required, such as inert materials,surfactants, solvents and other additives are equally known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd., Darland Books, Caldwell N.J.; H. v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley &Sons, N.Y.; Marschen, “Solvents Guide”, 2nd Ed., Interscience, N.Y.1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Technology], Volume 7, C. HauserVerlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active substances, fertilizers and/or growthregulators, for example in the form of a readymix or a tank mix.Wettable powders are preparations which are uniformly dispersible inwater and which contain, besides the active substance and in addition toa diluent or inert material, wetting agents, for example polyoxethylatedalkylphenols, polyoxethylated fatty alcohols, alkyl- oralkylphenolsulfonates, and dispersing agents, for example sodiumligninsulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate, or sodium oleylmethyltaurate.

Emulsifiable concentrates are prepared by dissolving the activesubstance in an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons,with addition of one or more emulsifiers. Examples of emulsifiers whichcan be used are: calcium salts of alkylarylsulfonates, such as calciumdodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acidpolyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycolethers, propylene oxide/ethylene oxide condensation products, alkylpolyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fattyacid esters or polyoxethylene sorbitol esters.

Dusts are obtained by grinding the active substance with finely dividedsolid substances, for example talc, natural clays such as kaolin,bentonite, pyrophyllite or diatomaceous earth. Granules can be preparedeither by atomizing the active substance onto adsorptive, granulatedinert material or by applying active substance concentrates onto thesurface of carrier materials such as sand or faolinites, or ofgranulated inert material, by means of adhesives, for example polyvinylalcohol or sodium polyacrylate, or alternatively mineral oils. Suitableactive substances can also be granulated in the fashion conventional forthe preparation of fertilizer granules, if desired as a mixture withfertilizers.

The active substance concentration in wettable powders is, for example,approximately 10 to 90% by weight, the remainder to 100% is composed ofconventional formulation components. In the case of emulsifiableconcentrates, the active substance concentration can be approximately 5to 80% by weight. Formulations in the form of dusts usually contain 5 to20% of active substance, sprayable solutions approximately 2 to 20% byweight. In the case of granules, the active substance content dependspartly on whether the active compound is liquid or solid and on whichgranulation auxiliaries, fillers, etc. are used.

In addition, the active substance formulations mentioned contain, ifappropriate, the adhesives, wetting agents, dispersants, emulsifiers,penetrants, solvents, fillers or carriers which are conventional in eachcase.

For use, the concentrates which exist in commercially available formare, if appropriate, diluted in the customary manner, for example usingwater in the case of wettable powders, emulsifiable concentrates,dispersions and also in the case of some microgranules. Preparations inthe form of a dust and granulated preparations as well as sprayablesolutions are customarily not further diluted with other inertsubstances before use.

The application rate required depends on the external conditions suchas, inter alia, temperature and humidity. It can vary within widelimits, for example between 0.001 and 10.0 kg/ha or more of activeingredient, but it is preferably between 0.005 and 5 kg/ha.

The active substances according to the invention may be present in theircommercially available formulations and in the application formsprepared from these formulations in the form of mixtures with otheractive substances such as insecticides, attractants, sterilants,acaricides, nematicides, fungicides, growth-regulating substances orherbicides.

The pesticides include, for example, phosphoric esters, carbamates,carboxylic esters, formamidines, tin compounds and substances producedby microorganisms. Preferred components for mixtures are

1. from the group comprising the phosphorus compounds acephate,azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos,bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos,chlorpyriphos-methyl, demeton, demeton-S-methyl,demeton-S-methyl-sulphone, dialifos, diazinon, dichlorvos, dicrotophos,

 O,O-1,2,2,2-tetrachloroethyl phosphorothioate (SD 208 304), dimethoate,disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos,fenitrothion, fensulfothion, fenthion, fonofos, formothion, heptenophos,isazophos, isothioate, isoxathion, malathion, methacrifos,methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim,pirimiphos-ethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos,prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos,terbufos, tetraclorvinphos, thiometon, triazophos, trichlorphon,vamidothion;

2. from the group comprising the carbamates aldicarb, 2-secbutylphenylmethylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, furathiocarb, isoprocarb, methomyl,5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, ethyl4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate(OK 135),1-methylthio-(ethylidenamino)-N-methyl-N-(morpholinothio)carbamate (UC51717);

3. from the group comprising the carboxylic esters allethrin,alphamethrin,5-benzyl-3-furylmethyl-(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidene-methyl)cyclopropanecarboxylate,bioallethrin, bioallethrin ((S)cyclopentyl isomer), bioresmethrin,biphenate,(RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl-(1RS)-trans-3-(4-tert.butylphenyl)-2,2-dimethylcyclopropanecarboxylate(NCI 85193), cycloprothrin, cyhalothrin, cypermethrin, cyphenothrin,deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin,fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer),permethrin, pheothrin ((R) isomer), d-pralethrin, pyrethrins (naturalproducts), resmethrin, tefluthrin, tetramethrin, tralomethrin;

4. from the group comprising the amidines amitraz, chlordimeform;

5. from the group comprising the tin compounds cyhexatin, fenbutatinoxide;

6. others abamectin, Bacillus thuringiensis, bensultap, binapacryl,bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate,chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930),chlorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470),cyromazin, ethylN-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzcarboximidate,DDT, dicofol,N-(N(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenylamino)carbonyl)-2,6-difluorobenzamide(XRD 473), diflubenzuron,N-(2,3-dihydro-3-methyl-1,3-thiazol-2-yliden)-2,4-xylidine, dinobuton,dinocap, endosulfan, ethofenprox,(4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)propyl)silane,(4-ethoxyphenyl)(3-(4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane,fenoxycarb, 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenylether (MTI 800) granulosis and nuclear polyhedrosis viruses,fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH,hexythiazox, hydramechylnon (AC 217300), ivermectin,2-nitromethyl-4,5-dihydro-6H-thiazine (SD 52618),2-nitromethyl-3,4-dihydrothiazole (SD 35651),2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477),propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam andtriflumuron.

The active substance content of the use forms prepared from thecommercially available formulations can be from 0.00000001 to 95% byweight of active substance, preferably between 0.00001 and 1% by weight.

Application is effected in a conventional fashion, matched to the useforms.

The active substances according to the invention are also suitable forcontrolling endo- and ectoparasites in the field of veterinary medicineor in the field of animal husbandry.

The active substances according to the invention are applied in a knownfashion, such as by oral administration in the form of, for example,tablets, capsules, potions or granules, by dermal administration in theform of, for example, dipping, spraying, pouring-on and spotting-on andpowdering, and also by parenteral administration in the form of, forexample, an injection.

The novel compounds of the formula I according to the invention canaccordingly also be employed particularly advantageously in livestockhusbandry (for example cattle, sheep, pigs and poultry such as chickens,geese etc.). In a preferred embodiment of the invention, the novelcompounds, if appropriate in suitable formulations (cf. above) and ifappropriate with the drinking water or feed, are administered orally tothe animals. Since they are excreted effectively in the feces, thedevelopment of insects in the feces of the animals can be prevented verysimply in this fashion. The dosages and formulations suitable in eachcase are particularly dependent on the type and stage of development ofthe livestock and also on the infestation pressure, and can easily bedetermined and laid down by conventional methods. In the case of cattle,the novel compounds can be employed, for example, at dosage rates of0.01 to 1 mg/kg of body weight.

The compounds of the formula I according to the invention are alsodistinguished by an outstanding fungicidal activity. Fungal pathogenswhich have already entered the plant tissue can be controlledsuccessfully in a curative manner. This is particularly important andadvantageous in the case of those fungal diseases which can no longer becontrolled effectively with the otherwise customary fungicides onceinfection has taken place. The spectrum of action of the claimedcompounds embraces a large number of various economically importantphyto-pathogenic fungi such as, for example, Pyricularia oryzae,Leptosphaeria nodorum, Drechslera teres, powdery mildew species,Venturia inaequalis, Botrytis cinerea, Pseudocercosporellaherpotrichoides, rusts as well as representatives of the Oomycetes suchas, for example, Phytophthora infestans and Plasmopara viticola.

Besides, the compounds according to the invention are also suitable foruse in industrial fields, for example as wood preservatives, aspreservatives in paints, in cooling lubricants for metalworking, or aspreservatives in drilling and cutting oils.

The invention also relates to agents which comprise the compounds of theformula I besides suitable formulation auxiliaries. The agents accordingto the invention generally comprise 1 to 95% by weight of the activesubstances of the formula I.

They can be formulated in various ways, depending on the prevailingbiological and/or chemico-physical parameters. The followingpossibilities are therefore suitable for formulation: wettable powders(WP), emulsifiable concentrates (EC), aqueous dispersions on oil orwater basis (SC), suspoemulsions (SC), dusts (DP), seed-dressing agents,granules in the form of water-dispersible granules (WG), ULVformulations, microcapsules, waxes or baits.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986;van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Ed.1972-73; K. Martens, “Spray Drying Handbook”, 3rd Ed. 1979, G. GoodwinLtd. London.

The formulation auxiliaries which are required, such as inert materials,surfactants, solvents and other additives are equally known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H. v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley &Sons, N.Y.; Marschen, “Solvents Guide”, 2nd Ed., Interscience, N.Y.1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Technology], Volume 7, C. HauserVerlag Munich, 4th Ed. 1986.

The active substances according to the invention can be employed, intheir commercially available formulations, either on their own or in theform of a combination with other fungicides known from the literature.

Fungicides which are known from the literature and which can be combinedaccording to the invention with the compounds of the formula (I) are,for example, the following products:

anilazine, benalaxyl, benodanil, benomyl, binapacryl, bitertanol,buthiobat, captafol, captan, carbendazim, carboxin, CGD-94240 F,chlobenzthiazone, chlorthalonil, cymoxanil, cyproconazole, cyprofuram,dichlofluanid, dichlomezin, dichlobutrazol, diethofencarb,difluconazole, dimethirimol, dimethomorph, diniconazole, dinocap,dithianon, dodemorph, dodine, edifenfos, ethirimol, etridazole,fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentinacetate, fentin hydroxide, fluaziram, fluobenzimine, fluorimide,flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum,fuberidazole, furalaxyl, furmecyclox, guazatine, hexa-conazole,imazalil, iprobenfos, iprodione, isoprothiolane, copper compounds suchas copper oxychloride, copper oxine, copper oxide, mancozeb, maneb,mepronil, metalaxyl, methasulfocarb, methfuroxam, myclobutanil, nabam,nitrothalidopropyl, nuarimol, ofurace, oxadixyl, oxycarboxin,penconazole, pencycuron, PP 696, probenazole, probinel, prochloraz,procymidon, propamocarb, propiconazole, prothiocarb, pyracarbolid,pyrifenox, pyroquilon, rabenzazole, sulfur, tebuconazole, thiabendazole,thiofanate-methyl, thiram, tolclofos-methyl, tolyl-fluanid, triadimefon,triadimenol, tricyclazole, tridemorph, triflumizol, triforine,vinchlozolin, zineb, sodium dodecylsulfonate, sodium dodecylsulfate,sodium C13/C15-alcohol ether sulfonate, sodium cetostearyl-phosphate,dioctyl sodium sulfosuccinate, sodium iso-propylnaphthalenesulfonate,sodium methylenebis-naphthalenesulfonate, cetyltrimethylammoniumchloride, salts of long-chain primary, secondary or tertiary amines,alkylpropylenamines, laurylpyrimidinium bromide, ethoxylated quaternizedfatty amines, alkyldimethylbenzylammonium chloride and1-hydroxyethyl-2-alkylimidazoline.

The abovementioned components for the combinations represent knownactive substances, most of which are described in GH. R Worthing, U. S.B. Walker, The Pesticide Manual, 7th Edition (1983), British CropProtection Council.

The active substance content of the use forms prepared from thecommercially available formulations can vary within wide ranges, theactive substance concentration of the use forms can be between 0.0001and 95% by weight of active substance, preferably between 0.001 and 1%by weight. They are used in a fashion matched to the use forms.

The following examples serve to illustrate the invention.

A. FORMULATION EXAMPLES

a) A dust is obtained by mixing 10 parts by weight of active substanceand 90 parts by weight of talc as inert material and comminuting themixture in a hammer mill.

b) A wettable powder which is readily dispersible in water is obtainedby mixing 25 parts by weight of active substance, 65 parts by weight ofkaolin-containing quartz as inert material, 10 parts by weight ofpotassium ligninsulfonate and 1 part by weight of sodiumoleoylmethyltaurate as wetting and dispersing agent, and grinding themixture in a pin-disk mill.

c) A dispersion concentrate which is readily dispersible in water isprepared by mixing 40 parts by weight of active substance with 7 partsby weight of a sulfo-succinic monoester, 2 parts by weight of a sodiumligninsulfonate and 51 parts by weight of water and grinding the mixturein a ball mill to a fineness of below 5 microns.

d) An emulsifiable concentrate can be prepared from 15 parts by weightof active substance, 75 parts by weight of cyclohexanone as solvent and10 parts by weight of oxethylated nonylphenol (10 EO) as emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of activesubstance and an inert granulate carrier material such as attapulgite,granulated pumice and/or quartz sand. It is expedient to use asuspension of the wettable powder of Example b) with a solids content of30%, which is sprayed onto the surface of attapulgite granules, andthese are dried and mixed intimately. The amount of the wettable powderis approx. 5% by weight and that of the inert carrier material approx.95% by weight of the finished granules.

B. BIOLOGICAL EXAMPLES (USE AS FUNGICIDE) Example 1

Barley plants in the 3-leaf stage are heavily inoculated with conidia ofpowdery mildew of barley (Erysiphe graminis f. sp. hordei) and placed ina greenhouse at 20° C. and a relative atmospheric humidity of 90-95%. 24hours after the inoculation, the plants are wetted uniformly with thecompounds listed in Table 1 at the active substance concentrations whichare indicated. After an incubation time of 10 days, the plants areexamined for incidence of powdery mildew of barley. The diseaseindicence is expressed in % of diseased leaf area, relative tountreated, 100% infected control plants.

Applied at 500 mg of active substance/l of spray mixture, the followingsubstances are found to suppress disease completely:

Compounds according to Example No. 9, 17, 25, 30, 55, 80, 93, 99, 100.

Example 2

Barley plants cv. “Igri” in the 2-leaf stage are treated to runoff pointwith an aqueous suspension of the claimed compounds.

After the spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Pyreno-phora teres and incubated for 16hours in a controlled-environment cabinet at a relative atmospherichumidity of 100%. The infected plants are subsequently grown on in thegreenhouse at 25° C. and a relative atmospheric humidity of 80%.

Approx. 1 week after the inoculation, the disease is evaluated and thedisease incidence is scored as diseased leaf area compared with theuntreated, 100% infected control.

Applied at 500 mg of active substance/l of spray mixture, the followingsubstances are found to suppress disease completely:

Compounds according to Example No. 2, 9, 10, 13, 14, 17, 25, 55, 80, 93,106.

Example 3

Wheat cv. “Jubilar” in the 2-leaf stage is treated to runoff point withaqueous suspensions of the claimed compounds.

After the spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Puccinia recondita. The dripping-wet plantsare placed for approx. 16 hours in a controlled-environment cabinet at20° C. and a relative atmospheric humidity of approx. 100%. They arethen grown on in a greenhouse at a temperature of 22-25° C. and arelative atmospheric humidity of 50-70%.

After an incubation time of approx. 2 weeks, the fungus sporulates onthe entire leaf area of the untreated control plants (100% infection),so that the test plants can be evaluated for disease. The diseaseincidence is expressed as diseased leaf area compared with theuntreated, infected control plants.

Applied at 500 mg of active substance/l of spray mixture, the followingsubstances are found to suppress disease completely:

Compounds according to Example No. 2, 9, 12, 17, 25, 30, 80, 93, 99.

BIOLOGICAL EXAMPLES (USE AS ACARICIDE/INSECTICIDE) Example 1

Field beans (Vicia faba) heavily populated with the black bean aphid(Aphis fabae) are sprayed with aqueous dilutions of wettable powderconcentrates with an active substance content of 250 ppm until the stageof beginning of runoff point is reached. The mortality of the aphids isdetermined after 3 days. A destruction of 100% can be achieved using thecompounds according to Example No. 2, 9, 13, 17, 19, 25, 30, 55, 80, 93,99, 106, 1741, 1749, 1750.

Example 2

Bean plants Phaseolus v.) are heavily populated with greenhouse spidermites (Tetranychus urticae, full population) were sprayed with theaqueous dilution of a wettable powder concentrate containing 250 ppm ofthe active substance in question.

The mortality of the mites was checked after 7 days. A destruction of100% was achieved using the following compounds:

Compounds according to Example No. 2, 9, 10, 17, 19, 25, 30, 55, 80, 93,94, 99, 106, 1741.

Example 3

Filter papers on which eggs of the large milkweed bug (Oncopeltusfasciatus) have been placed are treated with 0.5 ml portions of aqueousdilution of the test formulation. After the coating has dried on, thePetri dish is sealed, and the interior is kept at maximum atmospherichumidity. The dishes are kept at room temperature, and the oricidal andlarvicidal activities are determined after 7 days. At an activesubstance content of 250 ppm, a mortality of 100% was obtained with thefollowing compounds:

Compounds according to Example No. 2, 9, 10, 13, 17, 19, 25, 30, 55, 80,93, 95, 99, 106, 312, 1741, 1749, 1750.

Example 4

1 ml portions of the test formulation, emulsified in water, are applieduniformly to the inside of the lid and the bottom of a Petri dish and,when the coating has dried on, batches of 10 imagines of the commonhousefly (Musca domestica) are introduced. The dishes are sealed andthen kept at room temperature, the mortality of the test animals isdetermined after 3 hours. At 250 ppm (based on active substancecontent), the following preparations show a good activity (100%mortality) against the common housefly:

Compounds according to Example No. 9, 10, 17, 18, 19, 25, 55, 80, 93,99, 106, 1741, 1750.

Example 5

Rice seed is placed into glass culture dishes containing cotton wool andgerminated under moist conditions and, after the stem has grown to alength of approx. 8 cm, it is dipped together with the leaves into thetest solution. The test solution is allowed to run off from the treatedrice plants, and the plants are transferred to culture containers andpopulated with batches of 10 larvae (L3) of the species Nilaparvatalugens, the individual test concentrations being kept separate from eachother. After the sealed culture containers have been kept at 21° C., themortality of the cicada larvae can be determined after 4 days.

Under these test conditions, the compounds according to Example No. 9,25, 30, 93, 99, 432 have a 100% activity at a test concentration of 250ppm of the active ingredient.

Example 6

Wheat seed is pregerminated for 6 hours under water and then transferredto 10 ml glass test tubes and covered with in each case 2 ml of soil. 1ml of water is added, and the plants remain in the glass culture dishesat room temperature (21° C.) until they have grown to a height ofapprox. 3 cm. Diabrotica larvae of a medium stage (batches of 10specimens) are then transferred to the dishes and placed on the soiland, after 2 hours, 1 ml of the test liquid concentration to be testedis then pipetted onto the soil surface in the dishes.

After a standing time of 5 days under laboratory conditions (21° C.),the soil, or parts of the roots, are examined for live Diabroticalarvae, and the mortality is determined.

Under the test conditions mentioned, the compounds according to ExampleNo. 2, 17, 19, 25, 93, 99 displayed an effectiveness of up to 100% at atest concentration of 250 ppm of the active ingredient.

Example 7

In vitro test with tropical cattle ticks (Boophilus microplus)

The following experimental set-up allowed the activity of the claimedcompounds against ticks to be demonstrated:

To prepare a suitable preparation of active substance, the activesubstances were dissolved at a concentration of 10% (w/v) in a mixturecomposed of dimethylformamide (85 g), nonylphenol polyglycol ether (3 g)and oxethylated castor oil (7 g), and the resulting emulsionconcentrates were diluted with water to a test concentration of 500 ppm.

Batches of ten females of the tropical tick Boophilus microplus whichhad sucked themselves full were immersed for five minutes in theseactive substance dilutions. The ticks were subsequently dried on filterpaper and then attached, by their backs, to an adhesive film for thepurpose of oviposition. The ticks were kept in an incubator at 28° C.and an atmospheric humidity of 90%.

As a control, female ticks were merely immersed in water. The inhibitionof oviposition two weeks after the treatment was used to assess theeffectiveness. 100% mean that no ticks have deposited eggs, 0% meansthat all ticks have deposited eggs.

In this test, a 100% inhibition of oviposition was caused by each of thecompounds 10, 19, 30 and 106 at an active substance concentration of 500ppm.

PREPARATION EXAMPLES Example A4-(4-tert-Butylcyclohexylamino)-5-chloro-6-ethylpyrimidine

3.5 g (0.02 mol) of 4,5-dichloro-6-ethylpyrimidine and 7.8 g (0.05 mol)of 4-tert-butylcyclohexylamine were heated for two hours at 100° C.,without solvent. After the mixture had cooled to room temperature, itwas worked up using methylene chloride/water and the organic phase wasdried and concentrated. The product was chromatographed on silica gelusing petroleum ether/ethyl acetate 7:3 for further purification and forthe separation of the cis/trans isomers.

The trans-cyclohexylamino derivative is eluted first (0.8 g of yellowoil solidifies, m.p. 94-96°). After a mixed fraction, which wasdiscarded, pure cis-cyclohexylamino derivative was finally obtained (3.0g of yellow oil).

Preparation of 4-tert-butylcyclohexylamine 312 g of4-tert-butylcyclohexanone in 500 ml of ammonia-saturated methanol werehydrogenated at 100° C. and 100 bar in the presence of 10 g of Raneynickel. The catalyst was filtered off, the mixture was concentrated, andthe crude product was purified on a thin-layer evaporator (105°/0.5 mm).303 g of colorless liquid were obtained. The product is an isomermixture in which the cis-cyclohexylamine derivative prevails.

4-(cis-4-Phenyl-cyclohexyloxy)-5,6,7,8-tetrahydroquinazoline

0.5 g (16.7 mmol) of 80% NaH was added in portions to a solution of 1.85g (105 mmol) of cis-4-phenylcyclohexanol in 30 ml of absolute THF. Afterthis, the mixture was heated for 1 hour at 50° C., and 1.5 g (8.75 mmol)of 4-chloro-5,6,7,8-tetrahydroquinazoline, dissolved in 15 ml ofabsolute THF, were added dropwise. The reaction mixture was subsequentlyrefluxed for 2 hours. After the mixture has cooled to room temperature,it was poured into saturated NH₄Cl solution and this was extracted withether, and the combined organic phase was dried over MgSO₄. The solventwas evaporated in vacuo, and the residue (2.7 g) was purified by flashchromatography over silica gel, using n-hexane/ethyl acetate (2:1).Concentration gave 1.5 g (50.2% of theory), colorless crystals, m.p.109° C.

4-(N-Benzoyl-piperidyl-4-oxy)-5-methoxy-6-methoxymethyl-pyrimidine

2.9 g (14.3 mmol) of N-benzoyl-4-hydroxypiperidine (prepared byNaBH₄-reduction of N-benzoylpiperidine-4-one) were added to a suspensionof 0.66 g (22 mmol) of 80% NaH in THF. This was then heated for 1 hourat 35-40° C., and 2.50 g (13.3 mmol) of4-chloro-5-methoxy-6-methoxymethyl- pyrimidine were subsequently addedwithout dilution. The reaction mixture was heated for 5 hours at 40° C.,poured into a little saturated NH₄Cl solution and extracted 5 timesusing ethyl acetate. The combined organic phases were dried over MgSO₄,and the residue (3.4 g) was purified by flash chromatography over silicagel using ethyl acetate. Concentration gave 0.6 g (13% of theory) ofyellow oil, n_(D) ²⁰=1.5815.

More examples can be found in Tables I-IV below.

Abbreviations used T¹

T²

T³

T⁴

T⁵

T⁶

T⁷

T⁸

T⁹

T¹⁰

T¹¹

T¹²

T¹³

T¹⁴

T¹⁵

T¹⁶

T¹⁷

T¹⁸

T¹⁹

T²⁰

T²¹

T²²

T²³

T²⁴

T²⁵

T²⁶

T²⁷

T²⁸

T²⁹

T³⁰

T³¹

T³²

T³³

T³⁴

T³⁵

T³⁶

T³⁷

T³⁸

T³⁹

T⁴⁰

T⁴¹

T⁴²

T⁴³

T⁴⁴

T⁴⁵

T⁴⁶

T⁴⁷

T⁴⁸

T⁴⁹

T⁵⁰

T⁵¹

T⁵²

T⁵³

T⁵⁴

T⁵⁵

T⁵⁶

T⁵⁷

T⁵⁸

T⁵⁹

T⁶⁰

T⁶¹

T⁶²

T⁶³

T⁶⁴

T⁶⁵

T⁶⁶

T⁶⁷

T⁶⁸

T⁶⁹

T⁷⁰

T⁷¹

T⁷²

T⁷³

T⁷⁴

T⁷⁵

T⁷⁶

T⁷⁷

T⁷⁸

T⁷⁹

T⁸⁰

T⁸¹

T⁸²

T⁸³

T⁸⁴

T⁸⁵

T⁸⁶

T⁸⁷

T⁸⁸

T⁸⁹

T⁹⁰

T⁹¹

T⁹²

T⁹³

T⁹⁴

T⁹⁵

T⁹⁶

T⁹⁷

T⁹⁸

T⁹⁹

T¹⁰⁰

T¹⁰¹

T¹⁰²

T¹⁰³

T¹⁰⁴

T¹⁰⁵

T¹⁰⁶

T¹⁰⁷

T¹⁰⁸

T¹⁰⁹

T¹¹⁰

T¹¹¹

T¹¹²

T¹¹³

T¹¹⁴

T¹¹⁵

T¹¹⁶

T¹¹⁷

T¹¹⁸

T¹¹⁹

T¹²⁰

T¹²¹

T¹²²

T¹²³

T¹²⁴

T¹²⁵

T¹²⁶

T¹²⁷

T¹²⁸

T¹²⁹

T¹³⁰

T¹³¹

T¹³²

T¹³³

T¹³⁴

T¹³⁵

T¹³⁶

T¹³⁷

T¹³⁸

T¹³⁹

T¹⁴⁰

T¹⁴¹

T¹⁴²

T¹⁴³

T¹⁴⁴

T¹⁴⁵

T¹⁴⁶

T¹⁴⁷

T¹⁴⁸

T¹⁴⁹

T¹⁵⁰

T¹⁵¹

T¹⁵²

T¹⁵³

T¹⁵⁴

T¹⁵⁵

T¹⁵⁶

T¹⁵⁷

T¹⁵⁸

T¹⁵⁹

T¹⁶⁰

T¹⁶¹

T¹⁶²

T¹⁶³

T¹⁶⁴

T¹⁶⁵

T¹⁶⁶

T¹⁶⁷

T¹⁶⁸

T¹⁶⁹

T¹⁷⁰

T¹⁷¹

T¹⁷²

T¹⁷³

T¹⁷⁴

T¹⁷⁵

T¹⁷⁶

T¹⁷⁷

T¹⁷⁸

T¹⁷⁹

T¹⁸⁰

T¹⁸¹

T¹⁸²

T¹⁸³

T¹⁸⁴

T¹⁸⁵

T¹⁸⁶

T¹⁸⁷

T¹⁸⁸

T¹⁸⁹

T¹⁹⁰

T¹⁹¹

T¹⁹²

T¹⁹³

T¹⁹⁴

T¹⁹⁵

T¹⁹⁶

T¹⁹⁷

T¹⁹⁸

T¹⁹⁹

T²⁰⁰

T²⁰¹

T²⁰²

T²⁰³

T²⁰⁴

T²⁰⁵

T²⁰⁶

T²⁰⁷

T²⁰⁸

T²⁰⁹

T²¹⁰

T²¹¹

T²¹²

T²¹³

T²¹⁴

T²¹⁵

T²¹⁶

T²¹⁷

T²¹⁸

T²¹⁹

T²²⁰

T²²¹

T²²²

T²²³

T²²⁴

T²²⁵

T²²⁶

T²²⁷

T²²⁸

T²²⁹

T²³⁰

T²³¹

T²³²

T²³³

T²³⁴

T²³⁵

T²³⁶

T²³⁷

T²³⁸

T²³⁹

T²⁴⁰

T²⁴¹

T²⁴²

T²⁴³

T²⁴⁴

T²⁴⁵

T²⁴⁶

T²⁴⁷

T²⁴⁸

TABLE I

Example No. R¹ R² R³ X E Q M.p. [° C.] 1 H CH₂OCH₃ OCH₃ NH — T¹ 76-78 2H CH₂OCH₃ OCH₃ NH — T² oil 3 H CH₂OCH₃ OCH₃ NH — T³ oil 4 H CH₂OCH₃ OCH₃NH — T⁴ oil 5 H CH₂OCH₃ OCH₃ O — T⁴ 6 H —(CH₂)₄— O — T⁴ 7 H C₂H₅ Cl NH —T⁴ oil 8 H C₂H₅ Cl O — T⁴ 9 H CH₂OCH₃ OCH₃ NH — T⁵, cis/trans = 1:2 oil10 H —(CH₂)₄— NH T⁵, cis/trans = 2:1 oil 11 H —(CH₂)₄— O — T⁶ 104 12 HCH₂OCH₃ OCH₃ NH — T⁶ 76-77 13 H CH₂OCH₃ OCH₃ O — T⁶ oil 14 H C₂H₅ Cl NH— T⁶ 94-96 15 H C₂H₅ Cl O — T⁷ oil 16 H C₂H₅ Cl NH — T⁷ oil 17 H CH₂OCH₃OCH₃ NH — T⁷ oil 18 H CH₂OCH₃ OCH₃ O — T⁷ oil 19 H —(CH₂)₄— O — T⁷ oil20 CH₃ C₂H₅ Cl NH — T⁷ 21 CH₃ C₂H₅ Cl O — T⁷ 22 H CH₂OCH₃ OCH₃ NH CH₂ T⁵oil 23 H CH₂OCH₃ OCH₃ O ″ T⁵ oil 24 H —(CH₂)₄— O CH₂ T⁵ oil 25 H CH₂OCH₃OCH₃ NH H T⁸ oil 26 H CH₂OCH₃ OCH₃ O H T⁸ oil 27 H C₂H₅ Cl NH H T⁸ oil28 H C₂H₅ Cl O H T⁸ oil 29 H —(CH₂)₄— O H T⁸ oil 30 H CH₂OCH₃ OCH₃ NH HT⁹ oil 31 H CH₂OCH₃ OCH₃ O H T⁹ oil 32 H C₂H₅ Cl NH H T⁹ oil 33 H C₂H₅Cl O H T⁹ 34 H —(CH₂)₄— O H T⁹ oil 35 H CH₂OCH₃ OCH₃ NH H T¹⁰ oil 36 HCH₂OCH₃ OCH₃ O H T¹⁰ 37 H C₂H₅ Cl NH H T¹⁰ oil 38 H C₂H₅ Cl O H T¹⁰ 39 H—(CH₂)₄— O H T¹⁰ 40 H CH₂OCH₃ OCH₃ NH H T¹¹ oil 41 H CH₂OCH₃ OCH₃ O HT¹¹ 42 H —(CH₂)₄— O H T¹¹ 43 H C₂H₅ Cl NH — T¹¹ oil 44 H C₂H₅ Cl O — T¹¹45 H CH₂OCH₃ OCH₃ NH — T¹² 46 H CH₂OCH₃ OCH₃ O — T¹² 47 H C₂H₅ Cl NH —T¹² 48 H C₂H₅ Cl O — T¹² 49 H —(CH₂)₄— O — T¹² 50 H CH₂OCH₃ OCH₃ NH —T¹³ 51 H CH₂OCH₃ OCH₃ O — T¹³ 52 H C₂H₅ Cl NH — T¹³ 53 H C₂H₅ Cl O — T¹³54 H —(CH₂)₄ O — T¹³ oil 55 H CH₂OCH₃ OCH₃ NH — T¹⁴ oil 56 H CH₂OCH₃OCH₃ O — T¹⁴ 57 H C₂H₅ Cl NH — T¹⁴ 80-81 58 H C₂H₅ Cl O — T¹⁴ 59 H—(CH₂)₄— O — T¹⁴  69 60 H CH₂OCH₃ OCH₃ NH — T¹⁵ 78-80 61 CH₂OCH₃ OCH₃ O— T¹⁵ 62 C₂H₅ OCH₃ NH — T¹⁵ 63 C₂H₅ OCH₃ O — T¹⁵ 64 —(CH₂)₄— O — T¹⁵ 65CH₂OCH₃ OCH₃ NH — T¹⁶ 66 H CH₂OCH₃ OCH₃ O — T¹⁶ 67 H C₂H₅ Cl NH — T¹⁶ 68H C₂H₅ Cl O — T¹⁶ 69 H —(CH₂)₄— O — T¹⁶ 70 H CH₂OCH₃ Cl NH — T¹⁷ 71 HCH₂OCH₃ Cl O — T¹⁷ 72 H C₂H₅ Cl NH — T¹⁷ 73 H C₂H₅ Cl O — T¹⁷ 74 H—(CH₂)₄— O — T¹⁷ 75 H CH₂OCH₃ OCH₃ NH — T¹⁸ 69-70 76 H CH₂OCH₃ OCH₃ O —T¹⁸ 77 H C₂H₅ Cl NH — T¹⁸ 78 H C₂H₅ Cl O — T¹⁸ 79 H —(CH₂)₄— O — T¹⁸ 80H CH₂OCH₃ OCH₃ NH — T¹⁹ oil 81 H CH₂OCH₃ OCH₃ O — T¹⁹ oil 82 H C₂H₅ ClNH — T¹⁹ oil 83 H C₂H₅ Cl O — T¹⁹ 84 H —(CH₂)₄— O — T¹⁹ oil 85 H CH₂OCH₃OCH₃ NH CH₂ T⁵ oil 86 H CH₂OCH₃ OCH₃ O ″ T⁵ oil 87 —(CH₂)₄— O ″ T⁵ oil88 H CH₂OCH₃ OCH₃ NH CHCH₃ T²⁰ oil 89 H CH₂OCH₃ OCH₃ O ″ T²⁰ 90 H C₂H₅Cl NH ″ T²⁰ 91 H C₂H₅ Cl O ″ T²⁰ 92 H —(CH₂)₄— O — T²⁰ oil 93 H CH₂OCH₃OCH₃ NH — T²¹, cis/trans = 2:1 oil 94 H CH₂OCH₃ OCH₃ NH — T²² 70-72 95 HCH₂OCH₃ OCH₃ O — T²² 37 96 H C₂H₅ Cl NH — T²² 79-80 97 H —(CH₂)₄— NH —T²² 165-166 98 H —(CH₂)₄— O — T²² 112 99 H CH₂OCH₃ OCH₃ NH — T²³ 82-84100 H CH₂OCH₃ OCH₃ O — T²³ 109 101 H C₂H₅ Cl NH — T²³ 74-75 102 H C₂H₅Cl O — T²³ 103 CH₃ C₂H₅ Cl NH — T²³ 104 CH₃ C₂H₅ Cl O — T²³ 105 H—(CH₂)₄— NH — T²³ 121-123 106 H —(CH₂)₄)— O — T²³ 109 107 H C₂H₅ C₂H₅ O— T²³ 108 H CH₂OCH₃ OCH₃ NH — T²⁴ oil 109 H CH₂OCH₃ OCH₃ O — T²⁴ 110 HC₂H₅ Cl NH — T²⁴ 63-65 111 H C₂H₅ Cl O — T²⁴ 112 H —(CH₂)₄— O — T²⁴93-94 113 H CH₂OCH₃ OCH₃ NH — T²⁵ 114 H CH₂OCH₃ OCH₃ O — T²⁵ 115 H C₂H₅Cl NH — T²⁵ 116 H C₂H₅ Cl NH — T²⁵ 117 H —(CH₂)₄— O — T²⁵ 118 H CH₂OCH₃OCH₃ NH — T²⁶ 119 H CH₂OCH₃ OCH₃ O — T²⁶ 120 H C₂H₅ Cl NH — T²⁶ 121 HC₂H₅ Cl O — T²⁶ 122 H —(CH₂)₄— O — T²⁶ 123 H CH₂OCH₃ OCH₃ NH — T²⁷ 124 HCH₂OCH₃ OCH₃ O — T²⁷ 125 H C₂H₅ Cl NH — T²⁷ 126 H C₂H₅ Cl O — T²⁷ 127 H—(CH₂)₄— O — T²⁷ 128 H CH₂OCH₃ Cl NH — T²⁸ 129 H CH₂OCH₃ Cl O — T²⁸ 130H C₂H₅ Cl NH — T²⁸ 131 H C₂H₅ Cl O — T²⁸ 132 H —(CH₂)₄— O — T²⁸ 133 HCH₂OCH₃ OCH₃ NH — T²⁹ 134 H CH₂OCH₃ OCH₃ O — T²⁹ 135 H C₂H₅ Cl NH — T²⁹136 H C₂H₅ Cl NH — T²⁹ 137 H —(CH₂)₄— O — T²⁹ 138 H CH₂OCH₃ OCH₃ NH —T³⁰ oil 139 H C₂H₅ Cl NH — T³⁰ oil 140 H CH₂OCH₃ OCH₃ NH — T³¹ 141 HCH₂OCH₃ OCH₃ O — T³¹ 142 H C₂H₅ Cl NH — T³¹ 143 H C₂H₅ Cl O — T³¹ 144 H—(CH₂)₄— O — T³¹ 145 H CH₂OCH₃ OCH₃ NH — T³² 146 H CH₂OCH₃ OCH₃ O — T³²147 H C₂H₅ Cl NH — T³² 148 H C₂H₅ Cl O — T³² 149 H —(CH₂)₄— O — T³² 150H CH₂OCH₃ OCH₃ NH T³³ 151 H CH₂OCH₃ OCH₃ O T³³ 152 H C₂H₅ Cl NH T³³ 153H C₂H₅ Cl O T³³ 154 H —(CH₂)₄— O T³³ 155 H CH₂OCH₃ OCH₃ NH — T³⁴ oil 156H CH₂OCH₃ OCH₃ NH — T³⁵ oil 157 H CH₂OCH₃ OCH₃ O — T³⁵ 158 H C₂H₅ Cl NH— T³⁵ 159 H C₂H₅ Cl O — T³⁵ 160 H —(CH₂)₄— O — T³⁵ 161 H CH₂OCH₃ OCH₃ NH— T³⁶ 162 H CH₂OCH₃ OCH₃ O — T³⁶ 163 H C₂H₅ Cl NH — T³⁶ 164 H C₂H₅ Cl O— T³⁶ 165 H —(CH₂)₄— O — T³⁶ 166 H CH₂OCH₃ OCH₃ NH — T³⁷ 167 H CH₂OCH₃OCH₃ O — T³⁷ 168 H C₂H₅ Cl NH — T³⁷ 169 H C₂H₅ Cl O — T³⁷ 170 H —(CH₂)₄—O — T³⁷ 171 H CH₂OCH₃ OCH₃ NH — T³⁸ 172 H CH₂OCH₃ OCH₃ O — T³⁸ 173 HC₂H₅ Cl NH — T³⁸ 174 H C₂H₅ Cl O — T³⁸ 175 H —(CH₂)₄— O — T³⁸ 176 HCH₂OCH₃ OCH₃ NH — T³⁹ 177 H CH₂OCH₃ OCH₃ O — T³⁹ 178 H C₂H₅ Cl NH — T⁴⁰179 H C₂H₅ Cl O — T⁴⁰ 180 H —(CH₂)₄— O — T⁴⁰ 181 H CH₂OCH₃ OCH₃ NH — T⁴¹182 H CH₂OCH₃ OCH₃ O — T⁴¹ 183 H C₂H₅ Cl NH — T⁴¹ 184 H C₂H₅ Cl O — T⁴¹185 H —(CH₂)₄— O — T⁴¹ 186 H CH₂OCH₃ OCH₃ NH — T⁴² 187 H CH₂OCH₃ OCH₃ O— T⁴² 188 H C₂H₅ Cl NH — T⁴² 189 H C₂H₅ Cl O — T⁴² 190 H —(CH₂)₄— O —T⁴³ 191 H CH₂OCH₃ OCH₃ NH — T⁴³ 192 H CH₂OCH₃ OCH₃ NH — T⁴⁴ oil 193 HCH₂OCH₃ OCH₃ O — T⁴⁴ 194 H C₂H₅ Cl NH — T⁴⁴ 195 H C₂H₅ Cl O — T⁴⁴ 196 H—(CH₂)₄— O — T⁴⁴ 197 H CH₂OCH₃ OCH₃ NH — T⁴⁵ 198 H CH₂OCH₃ OCH₃ O — T⁴⁵199 H C₂H₅ Cl NH — T⁴⁵ 200 H C₂H₅ Cl O — T⁴⁵ 201 H —(CH₂)₄— O — T⁴⁵ 202H CH₂OCH₃ OCH₃ NH — T⁴⁶ 60-62 203 H CH₂OCH₃ OCH₃ NH — T⁴⁷ 204 H C₂H₅ ClNH — T⁴⁷ 205 H CH₂OCH₃ OCH₃ NH — T⁴⁸ 206 H C₂H₅ Cl NH — T⁴⁸ 207 HCH₂OCH₃ OCH₃ NH — T⁴⁹ 208 H CH₂OCH₃ OCH₃ NH — T⁵⁰ solid 209 H CH₂OCH₃OCH₃ O — T⁵⁰ 210 H C₂H₅ Cl NH — T⁵⁰ 211 H C₂H₅ Cl O — T⁵⁰ 212 H —(CH₂)₄—O — T⁵⁰ 213 H CH₂OCH₃ Cl NH — T⁵¹ 214 H CH₂OCH₃ Cl O — T⁵¹ 215 H C₂H₅ ClNH — T⁵¹ 216 H C₂H₅ Cl O — T⁵¹ 217 H —(CH₂)₄— O — T⁵¹ 218 CH₂OCH₃ OCH₃NH — T⁵² 219 CH₂OCH₃ OCH₃ O — T⁵² 220 H C₂H₅ Cl NH — T⁵² 221 H C₂H₅ Cl O— T⁵² 222 H —(CH₂)₄— O — T⁵² 223 H CH₂OCH₃ OCH₃ NH — T⁵³ 142-143 224 HCH₂OCH₃ OCH₃ O — T⁵³ oil 225 H —(CH₂)₄— O — T⁵³ 226 H CH₂OCH₃ OCH₃ NH —T⁵⁴ 83-85 227 H CH₂OCH₃ OCH₃ O — T⁵⁴ oil 228 H —(CH₂)₄— O — T⁵⁴  95-100229 H CH₂OCH₃ OCH₃ NH — T⁵⁵ 112-114 230 H CH₂OCH₃ OCH₃ NH — T⁵⁶ 231 HCH₂OCH₃ OCH₃ NH — T⁵⁷ 232 H CH₂OCH₃ OCH₃ O — T⁵⁷ 233 H C₂H₅ Cl NH — T⁵⁷234 H C₂H₅ Cl O — T⁵⁷ 235 H —(CH₂)₄— O — T⁵⁷ 236 H CH₂OCH₃ OCH₃ NH — T⁵⁸137-139 237 H CH₂OCH₃ OCH₃ O — T⁵⁸ 238 H C₂H₅ Cl NH — T⁵⁸ 239 H C₂H₅ ClO — T⁵⁸ 240 H —(CH₂)₄— O — T⁵⁸ 241 H CH₂OCH₃ OCH₃ NH — T⁵⁹ 84-85 242 HCH₂OCH₃ OCH₃ O — T⁵⁹ 243 H C₂H₅ Cl NH — T⁵⁹ 83-84 244 H C₂H₅ Cl O — T⁵⁹245 H —(CH₂)₄— NH — T⁵⁹ oil 246 H CH₂OCH₃ OCH₃ NH — T⁶⁰ 247 H CH₂OCH₃OCH₃ O — T⁶⁰ 248 H C₂H₅ Cl NH — T⁶⁰ 249 H C₂H₅ Cl O — T⁶⁰ 250 H —(CH₂)₄—O — T⁶⁰ 251 H CH₂OCH₃ OCH₃ NH — T⁶¹ 252 H CH₂OCH₃ OCH₃ O — T⁶¹ 253 HC₂H₅ Cl NH — T⁶¹ 254 H C₂H₅ Cl O — T⁶¹ 255 H —(CH₂)₄— O — T⁶¹ 256 HCH₂OCH₃ OCH₃ NH — T⁶² 95-96 257 H CH₂OCH₃ OCH₃ O — T⁶² 258 H C₂H₅ Cl NH— T⁶² 101-102 259 H C₂H₅ Cl O — T⁶² 260 H —(CH₂)₄— O — T⁶² 261 H CH₂OCH₃OCH₃ NH — T⁶³ 262 H CH₂OCH₃ OCH₃ O — T⁶³ 263 H C₂H₅ Cl NH — T⁶³ 81-83264 H C₂H₅ Cl O — T⁶³ 265 H —(CH₂)₄— O — T⁶³ 266 H CH₂OCH₃ OCH₃ NH — T⁶⁴267 H CH₂OCH₃ OCH₃ O — T⁶⁴ 268 H C₂H₅ Cl NH — T⁶⁴ 269 H C₂H₅ Cl O — T⁶⁴270 H —(CH₂)₄— — — T⁶⁴ 271 H CH₂OCH₃ OCH₃ NH — T⁶⁵ 272 H CH₂OCH₃ OCH₃ O— T⁶⁵ 273 H C₂H₅ Cl NH — T⁶⁵ 274 H C₂H₅ Cl O — T⁶⁵ 275 H —(CH₂)₄— O —T⁶⁵ 276 H CH₂OCH₃ Cl NH — T⁴ 277 H C₂C₅ Br NH — T⁴ 278 H C₂C₅ C₂C₅ NH —T⁴ 279 H CH₂OCH₃ Cl NH — T⁷ oil 280 H CH₂OCH₃ C₂C₅ NH — T⁷ oil 281 HCH₂OCH₃ H NH — T⁷ oil 282 H C₂H₅ C₂H₅ NH — T⁷ 283 H C₂H₅ Br NH — T⁷ 284H C₂H₅ F NH — T⁷ 285 H CH₃ Cl NH — T⁷ 286 H CH₃ OCH₃ NH — T⁷ 287 H C₂H₅OCH₃ NH — T⁷ 288 H CH(CH₃)₂ Cl NH — T⁷ 289 H cyclo- Cl NH — T⁷ propyl290 H C₂H₅ C₂H₅ NH — T⁸ 291 H C₂H₅ Br NH — T⁸ 292 H CH₂OCH₃ Cl NH — T⁸293 H C₂H₅ C₂H₅ NH — T⁹ 294 H CH₂OCH₃ Cl NH — T⁹ 295 H C₂H₅ Br NH — T⁹296 H C₂H₅ C₂H₅ NH — T¹⁰ 297 H C₂H₅ Br NH — T¹⁰ 298 H CH₂OCH₃ Cl NH —T¹⁰ 299 H C₂H₅ C₂H₅ NH — T¹¹ 300 H C₂H₅ C₂H₅ O — T¹¹ 301 H CH₂OCH₃ Cl NH— T¹¹ 302 H C₂H₅ Br NH — T¹¹ 303 H C₂H₅ C₂H₅ NH — T¹⁴ 304 H C₂H₅ C₂H₅ O— T¹⁴ 305 H CH₂OCH₃ Cl NH — T¹⁴ 306 H CH₂OCH₃ Cl NH — T²³ oil 307 HCH₂OCH₃ C₂H₅ NH — T²³ 78-79 308 H CH₂OCH₃ H NH — T²³ oil 309 H C₂H₅ C₂H₅NH — T²³ 310 H C₂H₅ I NH — T²³ 311 H C₂H₅ F NH — T²³ 312 H C₂H₅ F O —T²³ 313 H C₂H₅ Br NH — T²³ 314 H CH₃ Cl NH — T²³ 315 H (CH₂)₄ NH — T²⁴164-166 316 H CH₂OCH₃ OCH₃ NH — T⁶⁶ 317 H CH₂OCH₃ OCH₃ O — T⁶⁶ oil 318 HC₂H₅ Cl NH — T⁶⁶ 319 H C₂H₅ Cl O — T⁶⁶ oil 320 H (CH₂)₄ NH — T⁶⁶ 321 H(CH₂)₄ O — T⁶⁶ oil 322 H C₂C₅ C₂H₅ NH — T⁶⁶ 323 H CH₂OCH₃ Cl NH — T⁶⁶324 H CH₂OCH₃ OCH₃ NH — T⁶⁷ 325 H CH₂OCH₃ OCH₃ O — T⁶⁷ 326 H C₂H₅ Cl NH— T⁶⁷ 327 H C₂H₅ Cl O — T⁶⁷ 328 H (CH₂)₄ O — T⁶⁷ 329 H CH₂OCH₃ OCH₃ NH —T⁶⁸ oil 330 H CH₂OCH₃ OCH₃ O — T⁶⁸ oil 331 H C₂H₅ Cl NH — T⁶⁸ oil 332 HC₂H₅ Cl O — T⁶⁸ oil 333 H C₂H₅ C₂H₅ NH — T⁶⁸ 334 H C₂H₅ C₂H₅ O — T⁶⁸ 335H (CH₂)₄ NH — T⁶⁸ 336 H (CH₂)₄ O — T⁶⁸ oil 337 H C₂C₅ Br NH — T⁶⁸ 338 HC₂H₅ Br O — T⁶⁸ 339 H C₂H₅ F NH — T⁶⁸ 340 H C₂H₅ F O — T⁶⁸ 341 H CH₂OCH₃Cl NH — T⁶⁸ 342 H CH₂OCH₃ Cl O — T⁶⁸ 343 H CH₃ Cl NH — T⁶⁸ 344 H CH₂OCH₃OCH₃ NH — T⁶⁹ 345 H CH₂OCH₃ OCH₃ O — T⁶⁹ 346 H C₂H₅ Cl NH — T⁶⁹ 347 HC₂H₅ Cl NH — T⁶⁹ 348 H (CH₂)₄ NH — T⁶⁹ 349 H (CH₂)₄ O — T⁶⁹ 79-82 350 HC₂H₅ C₂H₅ NH — T⁶⁹ 351 H C₂H₅ C₂H₅ O — T⁶⁹ 352 H C₂H₅ Cl NH — T⁷⁰ 352 HC₂H₅ Cl O — T⁷⁰ oil 354 H CH₂OCH₃ OCH₃ NH — T⁷⁰ 355 H CH₂OCH₃ OCH₃ O —T⁷⁰ oil 356 H (CH₂)₄ O — T⁷⁰ oil 357 H CH₂OCH₃ OCH₃ NH — T⁷¹ oil 358 HCH₂OCH₃ OCH₃ O — T⁷¹ 359 H C₂H₅ Cl NH — T⁷¹ oil 360 H C₂H₅ Cl O — T⁷¹361 H (CH₂)₄ NH — T⁷¹ 362 H (CH₂)₄ O — T⁷¹ 363 H C₂H₅ C₂H₅ NH — T⁷¹ 364H C₂H₅ C₂H₅ O — T⁷¹ 365 H CH₂OCH₃ OCH₃ NH — T⁷² oil 366 H CH₂OCH₃ OCH₃ O— T⁷² 367 H C₂H₅ Cl NH — T⁷² 368 H C₂H₅ Cl O — T⁷² 369 H (CH₂)₄ NH — T⁷²370 H (CH₂)₄ O — T⁷² 371 H C₂H₅ C₂H₅ NH — T⁷² 372 H C₂H₅ C₂H₅ O — T⁷²373 H CH₂OCH₃ OCH₃ NH — T⁷³ 374 H CH₂OCH₃ OCH₃ O — T⁷³ 375 H C₂H₅ Cl NH— T⁷³ 376 H C₂H₅ Cl O — T⁷³ 377 H (CH₂)₄ O T⁷³ 378 H CH₂OCH₃ OCH₃ NH —T⁷⁴ 379 H CH₂OCH₃ OCH₃ O — T⁷⁴ oil 380 H C₂H₅ Cl NH — T⁷⁴ 381 H C₂H₅ ClO — T⁷⁴ 87 382 H (CH₂)₄ O — T⁷⁴ 86 383 H C₂H₅ Cl NH — T⁷⁵ 384 H CH₂OCH₃OCH₃ NH — T⁷⁶ oil 385 H CH₂OCH₃ OCH₃ O — T⁷⁶ oil 386 H C₂H₅ Cl NH — T⁷⁶oil 387 H C₂H₅ Cl O — T⁷⁶ 58 388 H (CH₂)₄ NH — T⁷⁶ 389 H (CH₂)₄ O — T⁷⁶ 99-100 390 H CH₂OCH₃ C₂H₅ NH — T⁷⁶ oil 391 H C₂H₅ C₂H₅ NH — T⁷⁶ 392 HC₂H₅ C₂H₅ O — T⁷⁶ 393 H CH₂OCH₃ Cl NH — T⁷⁶ 394 H C₂H₅ F NH — T⁷⁶ 395 HC₂H₅ Br NH — T⁷⁶ 396 H CH₃ Cl NH — T⁷⁶ 397 H C₂H₅ Cl NH — T⁷⁶ 73-75 398H (CH₂)₄ O — T⁷⁷ 83 399 H CH₂OCH₃ C₂H₅ NH — T⁷⁷ 90-92 400 H CH₂OCH₃ OCH₃NH — T⁷⁸ 401 H CH₂OCH₃ OCH₃ O — T⁷⁸ 402 H C₂H₅ Cl NH — T⁷⁸ oil 403 HC₂H₅ Cl O — T⁷⁸ oil 404 H (CH₂)₄ O — T⁷⁸ oil 405 H CH₂OCH₃ OCH₃ NH — T⁷⁹406 H C₂H₅ Cl NH — T⁷⁹ 78-79 407 H CH₂OCH₃ OCH₃ NH — T⁸⁰ 408 H CH₂OCH₃OCH₃ O — T⁸⁰ oil 409 H C₂H₅ Cl NH — T⁸⁰ oil 410 H C₂H₅ Cl O — T⁸⁰ oil411 H (CH₂)₄ O — T⁸⁰ oil 412 H C₂H₅ Cl NH — T⁸¹ 72-74 413 H C₂H₅ Cl O —T⁸¹ oil 414 H CH₂OCH₃ OCH₃ NH — T⁸² 415 H CH₂OCH₃ OCH₃ O — T⁸² oil 416 HC₂H₅ Cl NH — T⁸² 417 H C₂H₅ Cl O — T⁸² 65 418 H (CH₂)₄ O — T⁸² 68 419 HCH₂OCH₃ OCH₃ NH — T⁸⁴ 420 H CH₂OCH₃ OCH₃ O — T⁸⁴ 421 H C₂H₅ Cl NH — T⁸⁴422 H C₂H₅ Cl O — T⁸⁴ 423 H (CH₂)₄ O — T⁸⁴ 424 H CH₂OCH₃ OCH₃ NH T⁸⁵ 425H CH₂OCH₃ OCH₃ O T⁸⁵ 426 H C₂H₅ Cl NH T⁸⁵ 427 H C₂H₅ Cl O T⁸⁵ 428 H(CH₂)₄ O T⁸⁵ 429 H CH₂OCH₃ OCH₃ NH — T⁸⁶ 430 H CH₂OCH₃ OCH₃ O — T⁸⁶ 431H C₂H₅ Cl NH — T⁸⁶ 432 H C₂H₅ Cl O — T⁸⁶ 433 H (CH₂)₄ O — T⁸⁶ 434 HCH₂OCH₃ OCH₃ NH — T⁸⁷ 435 H CH₂OCH₃ OCH₃ O — T⁸⁷ oil 436 H C₂H₅ Cl NH —T⁸⁷ oil 437 H C₂H₅ Cl O — T⁸⁷ 57 438 H (CH₂)₄ O — T⁸⁷ 67 439 H C₂H₅ ClNH — T⁸⁸ 65-66 440 H CH₂OCH₃ OCH₃ NH — T⁸⁹ oil 441 H CH₂OCH₃ OCH₃ O —T⁸⁹ oil 442 H C₂H₅ Cl NH — T⁸⁹ oil 443 H C₂H₅ Cl O — T⁸⁹ 53 444 H (CH₂)₄O — T⁸⁹ 59 445 H CH₂OCH₃ OCH₃ NH — T⁹⁰ oil 446 H C₂H₅ OCH₃ NH — T⁹⁰63-65 447 H CH₂OCH₃ OCH₃ NH — T⁹¹ 448 H CH₂OCH₃ OCH₃ O — T⁹¹ 449 H C₂H₅Cl NH — T⁹¹ 450 H C₂H₅ Cl O — T⁹¹ 451 H (CH₂)₄ O — T⁹¹ 452 H CH₂OCH₃OCH₃ NH — T⁹² 453 H CH₂OCH₃ OCH₃ O — T⁹² 454 H C₂H₅ Cl NH — T⁹² 455 HC₂H₅ Cl O — T⁹² 456 H (CH₂)₄ NH — T⁹² 457 H CH₂OCH₃ OCH₃ O — T⁹³ 458 HCH₂OCH₃ OCH₃ NH — T⁹³ 459 H C₂H₅ Cl O — T⁹³ 460 H C₂H₅ Cl O — T⁹³ 461 H(CH₂)₄ NH — T⁹³ 462 H (CH₂)₄ O — T⁹³ 463 H CH₂OCH₃ OCH₃ NH — T⁹⁴ 464 HCH₂OCH₃ OCH₃ O — T⁹⁴ 465 H C₂H₅ Cl NH — T⁹⁴ oil 466 H C₂H₅ Cl O — T⁹⁴58-60 467 H (CH₂)₄ O — T⁹⁴ oil 468 H CH₂OCH₃ OCH₃ NH — T⁹⁵ 469 H CH₂OCH₃OCH₃ O — T⁹⁵ 470 H C₂H₅ Cl NH — T⁹⁵ oil 471 H C₂H₅ Cl O — T⁹⁵ oil 472 H(CH₂)₄ O — T⁹⁵ oil 473 H C₂H₅ Cl NH — T⁹⁶ oil 474 H CH₂OCH₃ OCH₃ NH —T⁹⁷ 475 H CH₂OCH₃ OCH₃ O — T⁹⁷ 476 H C₂H₅ Cl NH — T⁹⁷ 477 H C₂H₅ Cl O —T⁹⁷ 71 478 H (CH₂)₄ NH — T⁹⁷ 479 H (CH₂)₄ O — T⁹⁷ oil 480 H CH₂OCH₃ OCH₃NH — T⁹⁸ 481 H CH₂OCH₃ OCH₃ O — T⁹⁸ 482 H C₂H₅ Cl NH — T⁹⁸ 483 H C₂H₅ ClO — T⁹⁸ 484 H (CH₂)₄ O — T⁹⁸ oil 485 H CH₂OCH₃ OCH₃ NH — T⁹⁹ 486 HCH₂OCH₃ OCH₃ O — T⁹⁹ 487 H C₂H₅ Cl NH — T⁹⁹ 488 H C₂H₅ Cl O — T⁹⁹ 489 H(CH₂)₄ O — T⁹⁹ 490 H CH₂OCH₃ OCH₃ NH — T¹⁰⁰ 491 H CH₂OCH₃ OCH₃ O — T¹⁰⁰492 H C₂H₅ Cl NH — T¹⁰⁰ 493 H C₂H₅ Cl O — T¹⁰⁰ 494 H (CH₂)₄ O — T¹⁰⁰ 495H CH₂OCH₃ OCH₃ NH — T¹⁰¹ 496 H CH₂OCH₃ OCH₃ O — T¹⁰¹ 497 H C₂H₅ Cl NH —T¹⁰¹ 498 H C₂H₅ Cl O — T¹⁰¹ 499 H (CH₂)₄ O — T¹⁰¹ 500 H CH₂OCH₃ OCH₃ NH— T¹⁰² 501 H CH₂OCH₃ OCH₃ O — T¹⁰² 502 H C₂H₅ Cl NH — T¹⁰² 503 H C₂H₅ ClO — T¹⁰² 504 H (CH₂)₄ O — T¹⁰² 505 H CH₂OCH₃ OCH₃ NH — T¹⁰³ 506 HCH₂OCH₃ OCH₃ O — T¹⁰³ 507 H C₂H₅ Cl NH — T¹⁰³ 508 H C₂H₅ Cl O — T¹⁰³ 509H (CH₂)₄ O — T¹⁰³ 510 H CH₂OCH₃ OCH₃ NH — T¹⁰⁴ 511 H CH₂OCH₃ OCH₃ O —T¹⁰⁴ oil 512 H C₂H₅ Cl NH — T¹⁰⁴ 513 H C₂H₅ Cl O — T¹⁰⁴ 100-103 514 H(CH₂)₄ O — T¹⁰⁴ 108-112 515 H CH₂OCH₃ OCH₃ NH — T¹⁰⁵ 516 H CH₂OCH₃ OCH₃O − T¹⁰⁵ 517 H C₂H₅ Cl NH — T¹⁰⁵ 518 H C₂H₅ Cl O — T¹⁰⁵ 519 H (CH₂)₄ O —T¹⁰⁵ 520 H CH₂OCH₃ OCH₃ NH — T¹⁰⁶ 521 H CH₂OCH₃ OCH₃ O — T¹⁰⁶ 522 H C₂H₅Cl NH — T¹⁰⁶ 523 H C₂H₅ Cl O — T¹⁰⁶ 524 H (CH₂)₄ O — T¹⁰⁶ 525 H CH₂OCH₃OCH₃ NH — T¹⁰⁷ 526 H CH₂OCH₃ OCH₃ O — T¹⁰⁷ oil 527 H C₂H₅ Cl NH — T¹⁰⁷528 H C₂H₅ Cl O — T¹⁰⁷ oil 529 H (CH₂)₄ O — T¹⁰⁷ oil 530 H CH₂OCH₃ OCH₃NH — T¹⁰⁸ 531 H CH₂OCH₃ OCH₃ O — T¹⁰⁸ 532 H C₂H₅ Cl NH — T¹⁰⁸ 533 H C₂H₅Cl O — T¹⁰⁸ 534 H (CH₂)₄ O — T¹⁰⁸ 535 H CH₂OCH₃ OCH₃ NH — T¹⁰⁹ 536 HCH₂OCH₃ OCH₃ O — T¹⁰⁹ 537 H C₂H₅ Cl NH — T¹⁰⁹ 538 H C₂H₅ Cl O — T¹⁰⁹ 539H (CH₂)₄ O — T¹⁰⁹ 540 H CH₂OCH₃ OCH₃ NH — T¹¹⁰ 541 H CH₂OCH₃ OCH₃ O —T¹¹⁰ 542 H C₂H₅ Cl NH — T¹¹⁰ 543 H C₂H₅ Cl O — T¹¹⁰ 544 H (CH₂)₄ O —T¹¹⁰ 545 H CH₂OCH₃ OCH₃ NH — T¹¹¹ 546 H CH₂OCH₃ OCH₃ O — T¹¹¹ 547 H C₂H₅Cl NH — T¹¹¹ 548 H C₂H₅ Cl O — T¹¹¹ 549 H (CH₂)₄ O — T¹¹¹ 550 H CH₂OCH₃OCH₃ NH — T¹¹² 551 H CH₂OCH₃ OCH₃ O — T¹¹² 552 H C₂H₅ Cl NH — T¹¹² 553 HC₂H₅ Cl O — T¹¹² 554 H (CH₂)₄ O — T¹¹² oil 555 H CH₂OCH₃ OCH₃ NH — T¹¹³556 H CH₂OCH₃ OCH₃ O — T¹¹³ 557 H C₂H₅ Cl NH — T¹¹³ 558 H C₂H₅ Cl O —T¹¹³ 559 H (CH₂)₄ O — T¹¹³ 560 H CH₂OCH₃ OCH₃ NH — T¹¹⁴ 561 H CH₂OCH₃OCH₃ O — T¹¹⁴ 562 H C₂H₅ Cl NH — T¹¹⁴ 563 H C₂H₅ Cl O — T¹¹⁴ oil 564 H(CH₂)₄ O — T¹¹⁴ 565 H CH₂OCH₃ OCH₃ NH — T¹¹⁵ 566 H CH₂OCH₃ OCH₃ O — T¹¹⁵oil 567 H C₂H₅ Cl NH — T¹¹⁵ oil 568 H C₂H₅ Cl O — T¹¹⁵ 569 H (CH₂)₄ O —T¹¹⁵ oil 570 H C₂H₅ Cl NH — T¹¹⁶ oil 571 H CH₂OCH₃ OCH₃ NH — T¹¹⁷ 572 HCH₂OCH₃ OCH₃ O — T¹¹⁷ 573 H C₂H₅ Cl NH — T¹¹⁷ 574 H C₂H₅ Cl O — T¹¹⁷ 575H (CH₂)₄ O — T¹¹⁷ 576 H CH₂OCH₃ OCH₃ NH — T¹¹⁸ 577 H CH₂OCH₃ OCH₃ O —T¹¹⁸ oll 578 H C₂H₅ Cl NH — T¹¹⁸ 579 H C₂H₅ Cl O — T¹¹⁸ oil 580 H (CH₂)₄O — T¹¹⁸ oil 581 H CH₂OCH₃ OCH₃ NH — T¹¹⁹ 582 H CH₂OCH₃ OCH₃ O — T¹¹⁹583 H C₂H₅ Cl NH — T¹¹⁹ 584 H C₂H₅ Cl O — T¹¹⁹ 585 H (CH₂)₄ O — T¹¹⁹ 586H CH₂OCH₃ OCH₃ NH — T¹²⁰ 587 H CH₂OCH₃ OCH₃ O — T¹²⁰ 588 H C₂H₅ Cl NH —T¹²⁰ 589 H C₂H₅ Cl O — T¹²⁰ 590 H (CH₂)₄ O — T¹²⁰ 591 H CH₂OCH₃ OCH₃ NH— T¹²¹ 592 H CH₂OCH₃ OCH₃ O — T¹²¹ 593 H C₂H₅ Cl NH — T¹²¹ 594 H C₂H₅ ClO — T¹²¹ 595 H (CH₂)₄ O — T¹²¹ 596 H CH₂OCH₃ OCH₃ NH — T¹²² 597 HCH₂OCH₃ OCH₃ O — T¹²² 598 H C₂H₅ Cl NH — T¹²² 599 H C₂H₅ Cl O — T¹²² 600H (CH₂)₄ O — T¹²² 601 H CH₂OCH₃ OCH₃ NH — T¹²³ 602 H CH₂OCH₃ OCH₃ O —T¹²³ oil 603 H C₂H₅ Cl NH — T¹²³ 604 H C₂H₅ Cl O — T¹²³ 605 H (CH₂)₄ O —T¹²³ 63-73 606 H CH₂OCH₃ OCH₃ NH — T¹²⁴ 607 H CH₂OCH₃ OCH₃ O — T¹²⁴ 608H C₂H₅ Cl NH — T¹²⁴ 609 H C₂H₅ Cl O — T¹²⁴ 610 H (CH₂)₄ O — T¹²⁴ 611 HCH₂OCH₃ OCH₃ NH — T¹²⁵ 612 H CH₂OCH₃ OCH₃ O — T¹²⁵ 613 H C₂H₅ Cl NH —T¹²⁵ 614 H C₂H₅ Cl O — T¹²⁵ 615 H (CH₂)₄ O — T¹²⁵ 616 H CH₂OCH₃ OCH₃ NH— T¹²⁶ 617 H CH₂OCH₃ OCH₃ O — T¹²⁶ 618 H C₂H₅ Cl NH — T¹²⁶ 619 H C₂H₅ ClO — T¹²⁶ 620 H (CH₂)₄ O — T¹²⁶ 621 H CH₂OCH₃ OCH₃ NH — T¹²⁷ 622 HCH₂OCH₃ OCH₃ O — T¹²⁷ 623 H C₂H₅ Cl NH — T¹²⁷ 624 H C₂H₅ Cl O — T¹²⁷ 625H (CH₂)₄ O — T¹²⁷ 626 H CH₂OCH₃ OCH₃ NH — T¹²⁸ 627 H CH₂OCH₃ OCH₃ O —T¹²⁸ 628 H C₂H₅ Cl NH — T¹²⁸ 629 H C₂H₅ Cl O — T¹²⁸ 630 H (CH₂)₄ O —T¹²⁸ 631 H CH₂OCH₃ OCH₃ NH — T¹²⁹ 632 H CH₂OCH₃ OCH₃ O — T¹²⁹ 633 H C₂H₅Cl NH — T¹²⁹ 634 H C₂H₅ Cl O — T¹²⁹ 635 H (CH₂)₄ O — T¹²⁹ 636 H CH₂OCH₃OCH₃ NH — T¹³⁰ 637 H CH₂OCH₃ OCH₃ O — T¹³⁰ 638 H C₂H₅ Cl NH — T¹³⁰ 639 HC₂H₅ Cl O — T¹³⁰ 640 H (CH₂)₄ O — T¹³⁰ 641 H CH₂OCH₃ OCH₃ NH — T¹³¹ 642H CH₂OCH₃ OCH₃ O — T¹³¹ 643 H C₂H₅ Cl NH — T¹³¹ 644 H C₂H₅ Cl O — T¹³¹645 H (CH₂)₄ O — T¹³¹ 646 H CH₂OCH₃ OCH₃ NH — T¹³² 647 H CH₂OCH₃ OCH₃ O— T¹³² 648 H C₂H₅ Cl NH — T¹³² 649 H C₂H₅ Cl O — T¹³² 650 H (CH₂)₄ O —T¹³² 651 H CH₂OCH₃ OCH₃ NH — T¹³³ 652 H CH₂OCH₃ OCH₃ O — T¹³³ 653 H C₂H₅Cl NH — T¹³³ 654 H C₂H₅ Cl O — T¹³³ 655 H (CH₂)₄ O — T¹³³ 656 H CH₂OCH₃OCH₃ NH — T¹³⁴ 657 H CH₂OCH₃ OCH₃ O — T¹³⁴ 658 H C₂H₅ Cl NH — T¹³⁴ 659 HC₂H₅ Cl O — T¹³⁴ 660 H (CH₂)₄ O — T¹³⁴ 661 H CH₂OCH₃ OCH₃ NH — T¹³⁵ 662H CH₂OCH₃ OCH₃ O — T¹³⁵ 663 H C₂H₅ Cl NH — T¹³⁵ 664 H C₂H₅ Cl O — T¹³⁵665 H (CH₂)₄ O — T¹³⁵ 666 H CH₂OCH₃ OCH₃ NH — T¹³⁶ 667 H CH₂OCH₃ OCH₃ O— T¹³⁶ 668 H C₂H₅ Cl NH — T¹³⁶ 669 H C₂H₅ Cl O — T¹³⁶ 670 H (CH₂)₄ O —T¹³⁶ 671 H CH₂OCH₃ OCH₃ NH — T¹³⁷ 672 H CH₂OCH₃ OCH₃ O — T¹³⁷ 673 H C₂H₅Cl NH — T¹³⁷ 674 H C₂H₅ Cl O — T¹³⁷ 675 H (CH₂)₄ O — T¹³⁷ 676 H CH₂OCH₃OCH₃ NH — T¹³⁸ 677 H CH₂OCH₃ OCH₃ O — T¹³⁸ 678 H C₂H₅ Cl NH — T¹³⁸ 679 HC₂H₅ Cl O — T¹³⁸ 680 H (CH₂)₄ O — T¹³⁸ 681 H CH₂OCH₃ OCH₃ NH — T¹³⁹ 682H CH₂OCH₃ OCH₃ O — T¹³⁹ 683 H C₂H₅ Cl NH — T¹³⁹ 684 H C₂H₅ Cl O — T¹³⁹685 H (CH₂)₄ O — T¹³⁹ 686 H CH₂OCH₃ OCH₃ NH — T¹⁴⁰ 687 H CH₂OCH₃ OCH₃ O— T¹⁴⁰ 688 H C₂H₅ Cl NH — T¹⁴⁰ 689 H C₂H₅ Cl O — T¹⁴⁰ 690 H (CH₂)₄ O —T¹⁴⁰ 691 H CH₂OCH₃ OCH₃ NH — T¹⁴¹ 692 H CH₂OCH₃ OCH₃ O — T¹⁴¹ 693 H C₂H₅Cl NH — T¹⁴¹ 65-66 694 H C₂H₅ Cl O — T¹⁴¹ 695 H (CH₂)₄ O — T¹⁴¹ 696 HCH₂OCH₃ OCH₃ NH — T¹⁴² 697 H CH₂OCH₃ OCH₃ O — T¹⁴² 698 H C₂H₅ Cl NH —T¹⁴² 699 H C₂H₅ Cl O — T¹⁴² 700 H (CH₂)₄ O — T¹⁴² 701 H CH₂OCH₃ OCH₃ NH— T¹⁴³ 702 H CH₂OCH₃ OCH₃ O — T¹⁴³ 703 H C₂H₅ Cl NH — T¹⁴³ 704 H C₂H₅ ClO — T¹⁴³ 705 H (CH₂)₄ O — T¹⁴³ 706 H CH₂OCH₃ OCH₃ NH — T¹⁴⁴ 707 HCH₂OCH₃ OCH₃ O — T¹⁴⁴ 708 H C₂H₅ Cl NH — T¹⁴⁴ 709 H C₂H₅ Cl O — T¹⁴⁴ 710H (CH₂)₄ O — T¹⁴⁴ 711 H CH₂OCH₃ OCH₃ NH — T¹⁴⁵ 712 H CH₂OCH₃ OCH₃ O —T¹⁴⁵ 713 H C₂H₅ Cl NH — T¹⁴⁵ 714 H C₂H₅ Cl O — T¹⁴⁵ 715 H (CH₂)₄ O —T¹⁴⁵ 716 H CH₂OCH₃ OCH₃ NH — T¹⁴⁶ 717 H CH₂OCH₃ OCH₃ O — T¹⁴⁶ 718 H C₂H₅Cl NH — T¹⁴⁶ 719 H C₂H₅ Cl O — T¹⁴⁶ 720 H (CH₂)₄ O — T¹⁴⁶ 721 H CH₂OCH₃OCH₃ NH — T¹⁴⁷ 722 H CH₂OCH₃ OCH₃ O — T¹⁴⁷ 723 H C₂H₅ Cl NH — T¹⁴⁷ 724 HC₂H₅ Cl O — T¹⁴⁷ 725 H (CH₂)₄ O — T¹⁴⁷ 726 H CH₂OCH₃ OCH₃ NH — T¹⁴⁸ 727H CH₂OCH₃ OCH₃ O — T¹⁴⁸ 728 H C₂H₅ Cl NH — T¹⁴⁸ 729 H C₂H₅ Cl O — T¹⁴⁸730 H (CH₂)₄ O — T¹⁴⁸ 731 H CH₂OCH₃ OCH₃ NH — T¹⁴⁹ 732 H CH₂OCH₃ OCH₃ O— T¹⁴⁹ 733 H C₂H₅ Cl NH — T¹⁴⁹ 734 H C₂H₅ Cl O — T¹⁴⁹ 735 H (CH₂)₄ O —T¹⁴⁹ 736 H CH₂OCH₃ OCH₃ NH — T¹⁵⁰ 737 H CH₂OCH₃ OCH₃ O — T¹⁵⁰ 738 H C₂H₅Cl NH — T¹⁵⁰ 739 H C₂H₅ Cl O — T¹⁵⁰ 740 H (CH₂)₄ O — T¹⁵⁰ 741 H CH₂OCH₃OCH₃ NH — T¹⁵¹ 93-94 742 H CH₂OCH₃ OCH₃ O — T¹⁵¹ oil 743 H C₂H₅ Cl NH —T¹⁵¹ 110-111 744 H C₂H₅ Cl O — T¹⁵¹ 72 745 H (CH₂)₄ O — T¹⁵¹ 108 746 HCH₂OCH₃ OCH₃ NH — T¹⁵² oil 747 H CH₂OCH₃ OCH₃ O — T¹⁵² 748 H C₂H₅ Cl NH— T¹⁵² 87-88 749 H C₂H₅ Cl O — T¹⁵² 750 H (CH₂)₄ O — T¹⁵² 751 H CH₂OCH₃OCH₃ NH — T¹⁵³ 752 H CH₂OCH₃ OCH₃ O — T¹⁵³ 753 H C₂H₅ Cl NH — T¹⁵³ 754 HC₂H₅ Cl O — T¹⁵³ 755 H (CH₂)₄ O — T¹⁵³ 756 H CH₂OCH₃ OCH₃ NH — T¹⁵⁴ 757H CH₂OCH₃ OCH₃ O — T¹⁵⁴ 758 H C₂H₅ Cl NH — T¹⁵⁴ oil 759 H C₂H₅ Cl O —T¹⁵⁴ 760 H (CH₂)₄ O — T¹⁵⁴ 761 H CH₂OCH₃ OCH₃ NH — T¹⁵⁵ 762 H CH₂OCH₃OCH₃ O — T¹⁵⁵ 763 H C₂H₅ Cl NH — T¹⁵⁵ oil 764 H C₂H₅ Cl O — T¹⁵⁵ 765 H(CH₂)₄ O — T¹⁵⁵ 766 H CH₂OCH₃ OCH₃ NH — T¹⁵⁶ 767 H CH₂OCH₃ OCH₃ O — T¹⁵⁶768 H C₂H₅ Cl NH — T¹⁵⁶ 769 H C₂H₅ Cl O — T¹⁵⁶ 770 H (CH₂)₄ O — T¹⁵⁶ 771H CH₂OCH₃ OCH₃ NH — T¹⁵⁷ 772 H CH₂OCH₃ OCH₃ O — T¹⁵⁷ 773 H C₂H₅ Cl NH —T¹⁵⁷ 774 H C₂H₅ Cl O — T¹⁵⁷ 775 H (CH₂)₄ O — T¹⁵⁷ 776 H CH₂OCH₃ OCH₃ NH— T¹⁵⁸ 777 H CH₂OCH₃ OCH₃ O — T¹⁵⁸ 778 H C₂H₅ Cl NH — T¹⁵⁸ 779 H C₂H₅ ClO — T¹⁵⁸ 780 H (CH₂)₄ O — T¹⁵⁸ 781 H CH₂OCH₃ OCH₃ NH — T¹⁵⁹ 782 HCH₂OCH₃ OCH₃ O — T¹⁵⁹ 783 H C₂H₅ Cl NH — T¹⁵⁹ 784 H C₂H₅ Cl O — T¹⁵⁹ 785H (CH₂)₄ O — T¹⁵⁹ 786 H CH₂OCH₃ OCH₃ NH — T¹⁶⁰ oil 787 H CH₂OCH₃ OCH₃ O— T¹⁶⁰ 788 H C₂H₅ Cl NH — T¹⁶⁰ oil 789 H C₂H₅ Cl O — T¹⁶⁰ 790 H (CH₂)₄ O— T¹⁶⁰ 791 H CH₂OCH₃ OCH₃ NH — T¹⁶¹ oil 792 H CH₂OCH₃ OCH₃ O — T¹⁶¹ 793H C₂H₅ Cl NH — T¹⁶¹ oil 794 H C₂H₅ Cl O — T¹⁶¹ 795 H (CH₂)₄ O — T¹⁶¹ 796H CH₂OCH₃ OCH₃ NH — T¹⁶² 797 H CH₂OCH₃ OCH₃ O — T¹⁶² 798 H C₂H₅ Cl NH —T¹⁶² 799 H C₂H₅ Cl O — T¹⁶² 800 H (CH₂)₄ O — T¹⁶² 801 H CH₂OCH₃ OCH₃ NH— T¹⁶³ 802 H CH₂OCH₃ OCH₃ O — T¹⁶³ 803 H C₂H₅ Cl NH — T¹⁶³ 804 H C₂H₅ ClO — T¹⁶³ 805 H (CH₂)₄ O — T¹⁶³ 806 H CH₂OCH₃ OCH₃ NH — T¹⁶⁴ 807 HCH₂OCH₃ OCH₃ O — T¹⁶⁴ 808 H C₂H₅ Cl NH — T¹⁶⁴ 809 H C₂H₅ Cl O — T¹⁶⁴ 810H (CH₂)₄ O — T¹⁶⁴ 811 H CH₂OCH₃ OCH₃ NH — T¹⁶⁵ 812 H CH₂OCH₃ OCH₃ O —T¹⁶⁵ 813 H C₂H₅ Cl NH — T¹⁶⁵ 814 H C₂H₅ Cl O — T¹⁶⁵ 815 H (CH₂)₄ O —T¹⁶⁵ 816 H CH₂OCH₃ OCH₃ NH — T¹⁶⁶ 817 H CH₂OCH₃ OCH₃ O — T¹⁶⁶ 818 H C₂H₅Cl NH — T¹⁶⁶ 819 H C₂H₅ Cl O — T¹⁶⁶ 820 H (CH₂)₄ O — T¹⁶⁶ 821 H CH₂OCH₃OCH₃ NH — T¹⁶⁷ 822 H CH₂OCH₃ OCH₃ O — T¹⁶⁷ 823 H C₂H₅ Cl NH — T¹⁶⁷ 824 HC₂H₅ Cl O — T¹⁶⁷ 825 H (CH₂)₄ O — T¹⁶⁷ 826 H CH₂OCH₃ OCH₃ NH — T¹⁶⁸ 827H CH₂OCH₃ OCH₃ O — T¹⁶⁸ 828 H C₂H₅ Cl NH — T¹⁶⁸ 829 H C₂H₅ Cl O — T¹⁶⁸830 H (CH₂)₄ O — T¹⁶⁸ 831 H CH₂OCH₃ OCH₃ NH — T¹⁶⁹ 832 H CH₂OCH₃ OCH₃ O— T¹⁶⁹ 833 H C₂H₅ Cl NH — T¹⁶⁹ 834 H C₂H₅ Cl O — T¹⁶⁹ 835 H (CH₂)₄ O —T¹⁶⁹ 836 H CH₂OCH₃ OCH₃ NH — T¹⁷⁰ 837 H CH₂OCH₃ OCH₃ O — T¹⁷⁰ 838 H C₂H₅Cl NH — T¹⁷⁰ 839 H C₂H₅ Cl O — T¹⁷⁰ 840 H (CH₂)₄ O — T¹⁷⁰ 841 H CH₂OCH₃OCH₃ NH — T¹⁷¹ 842 H CH₂OCH₃ OCH₃ O — T¹⁷¹ 843 H C₂H₅ Cl NH — T¹⁷¹ 844 HC₂H₅ Cl O — T¹⁷¹ 845 H (CH₂)₄ O — T¹⁷¹ 846 H CH₂OCH₃ OCH₃ NH — T¹⁷² 847H CH₂OCH₃ OCH₃ O — T¹⁷² 848 H C₂H₅ Cl NH — T¹⁷² 849 H C₂H₅ Cl O — T¹⁷²850 H (CH₂)₄ O — T¹⁷² 851 H CH₂OCH₃ OCH₃ NH — T¹⁷³ 852 H CH₂OCH₃ OCH₃ O— T¹⁷³ 853 H C₂H₅ Cl NH — T¹⁷³ 854 H C₂H₅ Cl O — T¹⁷³ 855 H (CH₂)₄ O —T¹⁷³ 856 H CH₂OCH₃ OCH₃ NH — T¹⁷⁴ 857 H CH₂OCH₃ OCH₃ O — T¹⁷⁴ 858 H C₂H₅Cl NH — T¹⁷⁴ oil 859 H C₂H₅ Cl O — T¹⁷⁴ 860 H (CH₂)₄ O — T¹⁷⁴ 861 HCH₂OCH₃ OCH₃ NH — T¹⁷⁵ 862 H CH₂OCH₃ OCH₃ O — T¹⁷⁵ 863 H C₂H₅ Cl NH —T¹⁷⁵ oil 864 H C₂H₅ Cl O — T¹⁷⁵ 865 H (CH₂)₄ O — T¹⁷⁵ 866 H CH₂OCH₃ OCH₃NH — T¹⁷⁶ 867 H CH₂OCH₃ OCH₃ O — T¹⁷⁶ 868 H C₂H₅ Cl NH — T¹⁷⁶ 869 H C₂H₅Cl O — T¹⁷⁶ 870 H (CH₂)₄ O — T¹⁷⁶ 871 H CH₂OCH₃ OCH₃ NH — T¹⁷⁷ 872 HCH₂OCH₃ OCH₃ O — T¹⁷⁷ 873 H C₂H₅ Cl NH — T¹⁷⁷ 874 H C₂H₅ Cl O — T¹⁷⁷ 875H (CH₂)₄ O — T¹⁷⁷ 876 H CH₂OCH₃ OCH₃ NH — T¹⁷⁸ 877 H CH₂OCH₃ OCH₃ O —T¹⁷⁸ 878 H C₂H₅ Cl NH — T¹⁷⁸ 879 H C₂H₅ Cl O — T¹⁷⁸ 880 H (CH₂)₄ O —T¹⁷⁸ 881 H CH₂OCH₃ OCH₃ NH — T¹⁷⁹ 882 H CH₂OCH₃ OCH₃ O — T¹⁷⁹ 883 H C₂H₅Cl NH — T¹⁷⁹ 884 H C₂H₅ Cl O — T¹⁷⁹ 885 H (CH₂)₄ O — T¹⁷⁹ 886 H CH₂OCH₃OCH₃ NH — T¹⁸⁰ 887 H CH₂OCH₃ OCH₃ O — T¹⁸⁰ 888 H C₂H₅ Cl NH — T¹⁸⁰ oil889 H C₂H₅ Cl O — T¹⁸⁰ 890 H (CH₂)₄ O — T¹⁸⁰ 891 H CH₂OCH₃ OCH₃ NH —T¹⁸¹ 892 H CH₂OCH₃ OCH₃ O — T¹⁸¹ 893 H C₂H₅ Cl NH — T¹⁸¹ 894 H C₂H₅ Cl O— T¹⁸¹ 895 H (CH₂)₄ O — T¹⁸¹ 896 H CH₂OCH₃ OCH₃ NH — T¹⁸² 897 H CH₂OCH₃OCH₃ O — T¹⁸² 898 H C₂H₅ Cl NH — T¹⁸² 899 H C₂H₅ Cl O — T¹⁸² 900 H(CH₂)₄ O — T¹⁸² 901 H CH₂OCH₃ OCH₃ NH — T¹⁸³ 902 H CH₂OCH₃ OCH₃ O — T¹⁸³903 H C₂H₅ Cl NH — T¹⁸³ 904 H C₂H₅ Cl O — T¹⁸³ 905 H (CH₂)₄ O — T¹⁸³ 906H CH₂OCH₃ OCH₃ NH — T¹⁸⁴ 907 H CH₂OCH₃ OCH₃ O — T¹⁸⁴ 908 H C₂H₅ Cl NH —T¹⁸⁴ 909 H C₂H₅ Cl O — T¹⁸⁴ 910 H (CH₂)₄ O — T¹⁸⁴ 911 H CH₂OCH₃ OCH₃ NH— T¹⁸⁵ 912 H CH₂OCH₃ OCH₃ O — T¹⁸⁵ 913 H C₂H₅ Cl NH — T¹⁸⁵ 914 H C₂H₅ ClO — T¹⁸⁵ 915 H (CH₂)₄ O — T¹⁸⁵ 916 H CH₂OCH₃ OCH₃ NH — T¹⁸⁶ 917 HCH₂OCH₃ OCH₃ O — T¹⁸⁶ 918 H C₂H₅ Cl NH — T¹⁸⁶ oil 919 H C₂H₅ Cl O — T¹⁸⁶920 H (CH₂)₄ O — T¹⁸⁶ 921 H CH₂OCH₃ OCH₃ NH — T¹⁸⁷ 922 H CH₂OCH₃ OCH₃ O— T¹⁸⁷ 923 H C₂H₅ Cl NH — T¹⁸⁷ 924 H C₂H₅ Cl O — T¹⁸⁷ 925 H (CH₂)₄ O —T¹⁸⁷ 926 H CH₂OCH₃ OCH₃ NH — T¹⁸⁸ 927 H CH₂OCH₃ OCH₃ O — T¹⁸⁸ 928 H C₂H₅Cl NH — T¹⁸⁸ 929 H C₂H₅ Cl O — T¹⁸⁸ 930 H (CH₂)₄ O — T¹⁸⁸ 931 H CH₂OCH₃OCH₃ NH — T¹⁸⁹ 932 H CH₂OCH₃ OCH₃ O — T¹⁸⁹ 933 H C₂H₅ Cl NH — T¹⁸⁹ 934 HC₂H₅ Cl O — T¹⁸⁹ 935 H (CH₂)₄ O — T¹⁸⁹ 936 H CH₂OCH₃ OCH₃ NH — T¹⁹⁰ 937H CH₂OCH₃ OCH₃ O — T¹⁹⁰ 938 H C₂H₅ Cl NH — T¹⁹⁰ 939 H C₂H₅ Cl O — T¹⁹⁰940 H (CH₂)₄ O — T¹⁹⁰ 941 H CH₂OCH₃ OCH₃ NH — T¹⁹¹ 942 H CH₂OCH₃ OCH₃ O— T¹⁹¹ 943 H C₂H₅ Cl NH — T¹⁹¹ 944 H C₂H₅ Cl O — T¹⁹¹ 945 H (CH₂)₄ O —T¹⁹¹ 946 H CH₂OCH₃ OCH₃ NH — T¹⁹² 947 H CH₂OCH₃ OCH₃ O — T¹⁹² 948 H C₂H₅Cl NH — T¹⁹² 949 H C₂H₅ Cl O — T¹⁹² 950 H (CH₂)₄ O — T¹⁹² 951 H CH₂OCH₃OCH₃ NH — T¹⁹³ 952 H CH₂OCH₃ OCH₃ O — T¹⁹³ 953 H C₂H₅ Cl NH — T¹⁹³ 954 HC₂H₅ Cl O — T¹⁹³ 955 H (CH₂)₄ O — T¹⁹³ 956 H CH₂OCH₃ OCH₃ NH — T¹⁹⁴ 957H CH₂OCH₃ OCH₃ O — T¹⁹⁴ 958 H C₂H₅ Cl NH — T¹⁹⁴ 959 H C₂H₅ Cl O — T¹⁹⁴960 H (CH₂)₄ O — T¹⁹⁴ 961 H CH₂OCH₃ OCH₃ NH — T¹⁹⁵ 962 H CH₂OCH₃ OCH₃ O— T¹⁹⁵ 963 H C₂H₅ Cl NH — T¹⁹⁵ 964 H C₂H₅ Cl O — T¹⁹⁵ 965 H (CH₂)₄ O —T¹⁹⁵ 966 H CH₂OCH₃ OCH₃ NH — T¹⁹⁶ 967 H CH₂OCH₃ OCH₃ O — T¹⁹⁶ 968 H C₂H₅Cl NH — T¹⁹⁶ 969 H C₂H₅ Cl O — T¹⁹⁶ 970 H (CH₂)₄ O — T¹⁹⁶ 971 H CH₂OCH₃OCH₃ NH — T¹⁹⁷ 972 H CH₂OCH₃ OCH₃ O — T¹⁹⁷ 973 H C₂H₅ Cl NH — T¹⁹⁷ 974 HC₂H₅ Cl O — T¹⁹⁷ 975 H (CH₂)₄ O — T¹⁹⁷ 976 H CH₂OCH₃ OCH₃ NH — T¹⁹⁸ 977H CH₂OCH₃ OCH₃ O — T¹⁹⁸ 978 H C₂H₅ Cl NH — T¹⁹⁸ 979 H C₂H₅ Cl O — T¹⁹⁸980 H (CH₂)₄ O — T¹⁹⁸ 981 H CH₂OCH₃ OCH₃ NH — T¹⁹⁹ 982 H CH₂OCH₃ OCH₃ O— T¹⁹⁹ 983 H C₂H₅ Cl NH — T¹⁹⁹ 984 H C₂H₅ Cl O — T¹⁹⁹ 985 H (CH₂)₄ O —T¹⁹⁹ 986 H CH₂OCH₃ OCH₃ NH — T²⁰⁰ 987 H CH₂OCH₃ OCH₃ O — T²⁰⁰ 988 H C₂H₅Cl NH — T²⁰⁰ 989 H C₂H₅ Cl O — T²⁰⁰ 990 H (CH₂)₄ — O T²⁰⁰ 991 H CH₂OCH₃OCH₃ — NH T²⁰¹ 992 H CH₂OCH₃ OCH₃ — O T²⁰¹ 993 H C₂H₅ Cl — NH T²⁰¹ 994 HC₂H₅ Cl — O T²⁰¹ 995 H (CH₂)₄ — O T²⁰¹ 996 H C₂H₅ Cl — NH T⁴ 177-178 997H C₂H₅ Cl — NH T⁷ 177-178 998 H C₂H₅ I — NH T⁷ 999 H C₂H₅ I — NH T¹⁴1000 H (CH₂)₂CH₃ Cl — NH T²³ 1001 H C₂H₅ I — NH T⁷⁶ 1002 H CH₂OCH₃ OCH₃— NH T²⁰² 1003 H CH₂OCH₃ OCH₃ — O T²⁰² 1004 H C₂H₅ Cl — NH T²⁰² 1005 HC₂H₅ OCH₃ — O T²⁰² 1006 H (CH₂)₄ — O T²⁰² 1007 H CH₂OCH₃ OCH₃ NH — T²⁰³1008 H CH₂OCH₃ OCH₃ O — T²⁰³ 1009 H C₂H₅ Cl NH — T²⁰³ 1010 H C₂H₅ Cl O —T²⁰³ 1011 H (CH₂)₄ O — T²⁰³ 1012 H CH₂OCH₃ OCH₃ NH — T²⁰⁴ 1013 H CH₂OCH₃OCH₃ O — T²⁰⁴ 1014 H C₂H₅ Cl NH — T²⁰⁴ 1015 H C₂H₅ Cl O — T²⁰⁴ 1016 H(CH₂)₄ O — T²⁰⁴ 1017 H CH₂OCH₃ OCH₃ NH — T²⁰⁵ 1018 H CH₂OCH₃ OCH₃ O —T²⁰⁵ 1019 H C₂H₅ Cl NH — T²⁰⁵ 1020 H C₂H₅ Cl O — T²⁰⁵ 1021 H (CH₂)₄ O —T²⁰⁶ 1022 H CH₂OCH₃ OCH₃ NH — T²⁰⁶ 1023 H CH₂OCH₃ OCH₃ O — T²⁰⁶ 1024 HC₂H₅ Cl NH — T²⁰⁶ 1025 H C₂H₅ Cl O — T²⁰⁶ 1026 H (CH₂)₄ O — T²⁰⁶ 1027 HCH₂OCH₃ OCH₃ NH — T²⁰⁷ 1028 H CH₂OCH₃ OCH₃ O — T²⁰⁷ 1029 H C₂H₅ Cl NH —T²⁰⁷ 1030 H C₂H₅ Cl O — T²⁰⁷ 1031 H (CH₂)₄ O — T²⁰⁷ 1032 H CH₂OCH₃ OCH₃NH — T²⁰⁸ 1033 H CH₂OCH₃ OCH₃ O — T²⁰⁸ 1034 H C₂H₅ Cl NH — T²⁰⁸ 1035 HC₂H₅ Cl O — T²⁰⁸ 1036 H (CH₂)₄ O — T²⁰⁸ 1037 H CH₂OCH₃ OCH₃ NH — T²⁰⁹1038 H CH₂OCH₃ OCH₃ O — T²⁰⁹ 1039 H C₂H₅ Cl NH — T²⁰⁹ 1040 H C₂H₅ Cl O —T²⁰⁹ 1041 H (CH₂)₄ O — T²⁰⁹ 1042 H CH₂OCH₃ OCH₃ NH — T²¹⁰ 1043 H CH₂OCH₃OCH₃ O — T²¹⁰ 1044 H C₂H₅ Cl NH — T²¹⁰ 1045 H C₂H₅ Cl O — T²¹⁰ 1046 H(CH₂)₄ O — T²¹⁰ 1047 H CH₂OCH₃ OCH₃ NH — T²¹¹ 1048 H CH₂OCH₃ OCH₃ O —T²¹¹ 1049 H C₂H₅ Cl NH — T²¹¹ 1050 H C₂H₅ Cl O — T²¹¹ 1051 H (CH₂)₄ O —T²¹¹ 1052 H CH₂OCH₃ OCH₃ NH — T²¹² 1053 H CH₂OCH₃ OCH₃ O — T²¹² 1054 HC₂H₅ Cl NH — T²¹² 1055 H C₂H₅ Cl O — T²¹² 1056 H (CH₂)₄ O — T²¹² 1057 HCH₂OCH₃ OCH₃ NH — T²¹³ 1058 H CH₂OCH₃ OCH₃ — O T²¹³ 1059 H C₂H₅ Cl — NHT²¹³ 1060 H C₂H₅ Cl — O T²¹³ 1061 H (CH₂)₄ — O T²¹³ 1062 H CH₂OCH₃ OCH₃— NH T²¹⁴ 1063 H CH₂OCH₃ OCH₃ — O T²¹⁴ 1064 H C₂H₅ Cl — NH T²¹⁴ 1065 HC₂H₅ Cl — O T²¹⁴ 1066 H (CH₂)₄ — O T²¹⁴ 1067 H CH₂OCH₃ OCH₃ — NH T²¹⁵1068 H CH₂OCH₃ OCH₃ — O T²¹⁵ 1069 H C₂H₅ Cl — NH T²¹⁵ 1070 H C₂H₅ Cl — OT²¹⁵ 1071 H (CH₂)₄ — O T²¹⁵ 1072 H CH₂OCH₃ OCH₃ — NH T²¹⁶ 1073 H CH₂OCH₃OCH₃ — O T²¹⁶ 1074 H C₂H₅ Cl — NH T²¹⁶ 1075 H C₂H₅ Cl O — T²¹⁶ 1076 H(CH₂)₄ O — T²¹⁶ 1077 H CH₂OCH₃ OCH₃ NH — T²¹⁷ 1078 H CH₂OCH₃ OCH₃ O —T²¹⁷ 1079 H C₂H₅ Cl NH — T²¹⁷ 1080 H C₂H₅ Cl O — T²¹⁷ 1081 H (CH₂)₄ O —T²¹⁷ 1082 H CH₂OCH₃ OCH₃ NH — T²¹⁸ 1083 H CH₂OCH₃ OCH₃ O — T²¹⁸ 1084 HC₂H₅ Cl NH — T²¹⁸ 1085 H C₂H₅ Cl O — T²¹⁸ 1086 H (CH₂)₄ O — T²¹⁸ 1087 HCH₂OCH₃ OCH₃ NH — T²¹⁹ 1088 H CH₂OCH₃ OCH₃ O — T²¹⁹ 1089 H C₂H₅ Cl NH —T²¹⁹ 1090 H C₂H₅ Cl O — T²¹⁹ 1091 H (CH₂)₄ O — T²¹⁹ 1092 H CH₂OCH₃ OCH₃NH — T²²⁰ 1093 H CH₂OCH₃ OCH₃ O — T²²⁰ 1094 H C₂H₅ Cl NH — T²²⁰ 1095 HC₂H₅ Cl O — T²²⁰ 1096 H (CH₂)₄ O — T²²⁰ 1097 H CH₂OCH₃ OCH₃ NH — T²²¹1098 H CH₂OCH₃ OCH₃ O — T²²¹ 1099 H C₂H₅ Cl NH — T²²¹ 1100 H C₂H₅ Cl O —T²²¹ 1101 H (CH₂)₄ O — T²²¹ 1102 H CH₂OCH₃ OCH₃ NH — T²²² 1103 H CH₂OCH₃OCH₃ O — T²²² 1104 H C₂H₅ Cl NH — T²²² 1105 H C₂H₅ Cl O — T²²² 1106 H(CH₂)₄ O — T²²² 1107 H CH₂OCH₃ OCH₃ NH — T²²³ 1108 H CH₂OCH₃ OCH₃ O —T²²³ 1109 H C₂H₅ Cl NH — T²²³ 1110 H C₂H₅ Cl O — T²²³ 1111 H (CH₂)₄ O —T²²³ 1112 H CH₂OCH₃ OCH₃ NH — T²²⁵ 1113 H CH₂OCH₃ OCH₃ O — T²²⁵ 1114 HC₂H₅ Cl NH — T²²⁵ 1115 H C₂H₅ Cl O — T²²⁵ 1116 H (CH₂)₄ O — T²²⁵ 1117 HCH₂OCH₃ OCH₃ NH — T²²⁶ 1118 H CH₂OCH₃ OCH₃ O — T²²⁶ 1119 H C₂H₅ Cl NH —T²²⁶ 1120 H C₂H₅ Cl O — T²²⁶ 1121 H (CH₂)₄ O — T²²⁶ 1122 H CH₂OCH₃ OCH₃NH — T²²⁷ 1123 H CH₂OCH₃ OCH₃ O — T²²⁷ 1124 H C₂H₅ Cl NH — T²²⁷ 1125 HC₂H₅ Cl O — T²²⁷ 1126 H (CH₂)₄ O — T²²⁷ 1127 H CH₂OCH₃ OCH₃ NH — T²²⁸1128 H CH₂OCH₃ OCH₃ O — T²²⁸ 1129 H C₂H₅ Cl NH — T²²⁸ 1130 H C₂H₅ Cl O —T²²⁸ 1131 H (CH₂)₄ O — T²²⁸ 1132 H CH₂OCH₃ OCH₃ NH — T²²⁹ 1133 H CH₂OCH₃OCH₃ O — T²²⁹ 1134 H C₂H₅ Cl NH — T²²⁹ 1135 H C₂H₅ Cl O — T²²⁹ 1136 H(CH₂)₄ O — T²²⁹ 1137 H CH₂OCH₃ OCH₃ NH — T²³⁰ 1138 H CH₂OCH₃ OCH₃ O —T²³⁰ 1139 H C₂H₅ Cl NH — T²³⁰ 1140 H C₂H₅ Cl O — T²³⁰ 1141 H (CH₂)₄ O —T²³⁰ 1142 H CH₂OCH₃ OCH₃ NH — T²³¹ 1143 H CH₂OCH₃ OCH₃ O — T²³¹ 1144 HC₂H₅ Cl NH — T²³¹ 1145 H C₂H₅ Cl O — T²³¹ 1146 H (CH₂)₄ O — T²³¹ 1147 HCH₂OCH₃ OCH₃ NH — T²³² 1148 H CH₂OCH₃ OCH₃ O — T²³² 1149 H C₂H₅ Cl NH —T²³² 1150 H C₂H₅ Cl O — T²³² 1151 H (CH₂)₄ O — T²³² 1152 H CH₂OCH₃ OCH₃NH — T²³³ 1153 H CH₂OCH₃ OCH₃ O — T²³³ 1154 H C₂H₅ Cl NH — T²³³ 1155 HC₂H₅ Cl O — T²³³ 1156 H (CH₂)₄ O — T²³³ 1157 H CH₂OCH₃ OCH₃ NH — T²³⁴1158 H CH₂OCH₃ OCH₃ O — T²³⁴ 1159 H C₂H₅ Cl NH — T²³⁴ 1160 H C₂H₅ Cl O —T²³⁴ 1161 H (CH₂)₄ O — T²³⁴ 1162 H CH₂OCH₃ OCH₃ NH — T²³⁵ 1163 H CH₂OCH₃OCH₃ O — T²³⁵ 1164 H C₂H₅ Cl NH — T²³⁵ 1165 H C₂H₅ Cl O — T²³⁵ 1166 H(CH₂)₄ O — T²³⁵ 1167 H CH₂OCH₃ OCH₃ NH — T²³⁶ 1168 H CH₂OCH₃ OCH₃ O —T²³⁶ 1169 H C₂H₅ Cl NH — T²³⁶ 1170 H C₂H₅ Cl O — T²³⁶ 1171 H (CH₂)₄ O —T²³⁶ 1172 H CH₂OCH₃ OCH₃ NH — T²³⁷ 1173 H CH₂OCH₃ OCH₃ O — T²³⁷ 1174 HC₂H₅ Cl NH — T²³⁷ 1175 H C₂H₅ Cl O — T²³⁷ 1176 H (CH₂)₄ O — T²³⁷ 1177 HCH₂OCH₃ OCH₃ NH — T²³⁸ 1178 H CH₂OCH₃ OCH₃ O — T²³⁸ 1179 H C₂H₅ Cl NH —T²³⁸ 1180 H C₂H₅ Cl O — T²³⁸ 1181 H (CH₂)₄ O — T²³⁸ 1182 H CH₂OCH₃ OCH₃NH — T²³⁹ 1183 H CH₂OCH₃ OCH₃ O — T²³⁹ 1184 H C₂H₅ Cl NH — T²³⁹ 1185 HC₂H₅ Cl O — T²³⁹ 1186 H (CH₂)₄ O — T²³⁹ 1187 H CH₂OCH₃ OCH₃ NH — T²⁴⁰1188 H CH₂OCH₃ OCH₃ O — T²⁴⁰ 1189 H C₂H₅ Cl NH — T²⁴⁰ 1190 H C₂H₅ Cl O —T²⁴⁰ 1191 H (CH₂)₄ O — T²⁴⁰ 1192 H CH₂OCH₃ OCH₃ NH — T²⁴¹ 1193 H CH₂OCH₃OCH₃ O — T²⁴¹ 1194 H C₂H₅ Cl NH — T²⁴¹ 1195 H C₂H₅ Cl O — T²⁴¹ 1196 H(CH₂)₄ O — T²⁴¹ 1197 H CH₂OCH₃ OCH₃ NH — T²⁴² 1198 H CH₂OCH₃ OCH₃ O —T²⁴² 1199 H C₂H₅ Cl NH — T²⁴² 1200 H C₂H₅ Cl O — T²⁴² 1201 H (CH₂)₄ O —T²⁴² 1202 H CH₂OCH₃ OCH₃ NH — T²⁴³ 1203 H CH₂OCH₃ OCH₃ O — T²⁴³ 1204 HC₂H₅ Cl NH — T²⁴³ 1205 H C₂H₅ Cl O — T²⁴³ 1206 H (CH₂)₄ O — T²⁴³ 1207 HCH₂OCH₃ OCH₃ NH — T²⁴⁴ 1208 H CH₂OCH₃ OCH₃ O — T²⁴⁴ 1209 H C₂H₅ Cl NH —T²⁴⁴ 1210 H C₂H₅ Cl O — T²⁴⁴ 1211 H (CH₂)₄ O — T²⁴⁴ 1212 H CH₂OCH₃ OCH₃NH — T²⁴⁵ 1213 H CH₂OCH₃ OCH₃ O — T²⁴⁵ 1214 H C₂H₅ Cl NH — T²⁴⁵ 1215 HC₂H₅ Cl O — T²⁴⁵ 1216 H (CH₂)₄ O — T²⁴⁵ 1217 H CH₂OCH₃ OCH₃ NH — T²⁴⁶1218 H CH₂OCH₃ OCH₃ O — T²⁴⁶ 1219 H C₂H₅ Cl NH — T²⁴⁶ 1220 H C₂H₅ Cl O —T²⁴⁶ 1221 H (CH₂)₄ O — T²⁴⁶ 1222 H CH₂OCH₃ OCH₃ NH — T²⁴⁷ 1223 H CH₂OCH₃OCH₃ O — T²⁴⁷ 1224 H C₂H₅ Cl NH — T²⁴⁷ 1225 H C₂H₅ Cl O — T²⁴⁷ 1226 H(CH₂)₄ O — T²⁴⁷ 1227 H CH₂OCH₃ OCH₃ NH — T²⁴⁸ 1228 H CH₂OCH₃ OCH₃ O —T²⁴⁸ 1229 H C₂H₅ Cl NH — T²⁴⁸ 1230 H C₂H₅ Cl O — T²⁴⁸ 1231 H (CH₂)₄ O —T²⁴⁸

TABLE II

Example No. R⁷ R⁸ R⁹ R¹⁰ X E Q M.p. [° C.] 1232 H H H H NH — T⁷ 135-1371233 H H H H O — T⁷ 1234 H Cl H H NH — T⁷ 1235 H Cl H H O — T⁷ 1236 H HCl H NH — T⁷ 1237 H H Cl H O — T⁷ 1238 CH₃ H H H NH — T⁷ 1239 CH₃ H H HO — T⁷ 1240 H H CH₃ H NH — T⁷ 1241 H H CH₃ H O — T⁷ 1242 H H H CH₃ NH —T⁷ 1243 H H H CH₃ O — T⁷ 1244 H H H H NH — T⁶ 140-142 1245 H H H H NH —T⁹ 90-92 1246 H H H H O — T⁹ oil 1247 H H H H NH — T⁸ 143-145 1248 H H HH O — T⁸ 1249 H H H H NH — T⁴ 158-160 1250 H H H H O — T⁴ 1251 H H H HNH — T¹⁰ 1252 H H H H O — T¹⁰ 1253 H H H H NH — T¹¹ 1254 H H H H O — T¹¹1255 H H H H NH — T¹² 1256 H H H H O — T¹² 1257 H H H H NH — T¹⁴ 1258 HH H H O — T¹⁴ 1259 H H H H NH — T²² 210-211 1260 H H H H NH — T²³153-155 1261 H H H H O — T²³ 1262 H H H H NH — T²³ 1263 F H H H O — T²³1264 H H Cl H NH — T²³ 1265 H H Cl H O — T²³ 1266 Cl H H H NH — T²³ 1267Cl H H H O — T²³ 1268 H H CH₃ H NH — T²³ 1269 H H CH₃ H O — T²³ 1270 H HH CH₃ NH — T²³ 1271 H H H CH₃ O — T²³ 1272 H H H H NH — T⁵⁸ 184-185 1273H H H H NH — T¹³ 1274 H H H H O — T¹³ 1275 H H H H NH — T¹⁶ 1276 H H H HO — T¹⁶ 1277 H H H H NH — T¹⁷ 1278 H H H H O — T¹⁷ 1279 H H H H NH — T¹⁹1280 H H H H O — T¹⁹ 1281 H H H H NH — T²⁴ 155-157 1282 H H H H O — T²⁴1283 H H H H NH — T²⁵ 1284 H H H H O — T²⁵ 1285 H H H H NH — T²⁶ 1286 HH H H O — T²⁶ 1287 H H H H NH — T²⁷ 1288 H H H H O — T²⁷ 1289 H H H H NH— T²⁸ 1290 H H H H O — T²⁸ 1291 H H H H NH — T²⁹ 1292 H H H H O — T²⁹1293 H H H H NH — T³⁰ 1294 H H H H O — T³⁰ 1295 H H H H NH — T³¹ 1296 HH H H O — T³¹ 1297 H H H H NH — T³² 1298 H H H H O — T³² 1299 H H H H NH— T³³ 1300 H H H H O — T³³ 1301 H H H H NH — T³⁴ 1302 H H H H O — T³⁴1303 H H H H NH — T³⁵ 1304 H H H H O — T³⁵ 1305 H H H H NH — T³⁶ 1306 HH H H O — T³⁶ 1307 H H H H NH — T³⁷ 1308 H H H H O — T³⁷ 1309 H H H H NH— T³⁸ 1310 H H H H O — T³⁸ 1311 H H H H NH — T³⁹ 1312 H H H H O — T³⁹1313 H H H H NH — T⁴⁰ 1314 H H H H O — T⁴⁰ 1315 H H H H NH — T⁴¹ 1316 HH H H O — T⁴¹ 1317 H H H H NH — T⁴² 1318 H H H H O — T⁴² 1319 H H H H NH— T⁴⁴ 1320 H H H H O — T⁴⁴ 1321 H H H H NH — T⁴⁵ 1322 H H H H O — T⁴⁵1323 H H H H NH — T⁴⁷ 1324 H H H H O — T⁴⁷ 1325 H H H H NH — T⁵⁰ 1326 HH H H O — T⁵⁰ 1327 H H H H NH — T⁵¹ 1328 H H H H O — T⁵¹ 1329 H H H H NH— T⁵² 1330 H H H H O — T⁵² 1331 H H H H NH — T⁵⁴ 1332 H H H H O — T⁵⁴1333 H H H H NH — T⁵⁵ 1334 H H H H O — T⁵⁵ 121 1335 H H H H NH — T⁵⁶1336 H H H H O — T⁵⁶ 1337 H H H H NH — T⁵⁹ 144-145 1338 H H H H O — T⁵⁹1339 H H H H NH — T⁶⁰ 1340 H H H H O — T⁶⁰ 1341 H H H H NH — T⁶¹ 1342 HH H H O — T⁶¹ 1343 H H H H NH — T⁶² 176 1344 H H H H O — T⁶² 117 1345 HH H H NH — T⁶⁶ 1346 H H H H O — T⁶⁶ oil 1347 H H H H NH — T⁶⁷ 1348 H H HH O — T⁶⁷ 1349 H H H H NH — T⁶⁸ glass 1350 H H H H O — T⁶⁸ oil 1351 H HH H NH — T⁶⁹ 1352 H H H H O — T⁶⁹ 69-72 1353 H H H H NH — T⁷⁰ 1354 H H HH O — T⁷⁰ 1355 H H H H NH — T⁷² 1356 H H H H O — T⁷² 1357 H H H H NH —T⁷³ 1358 H H H H O — T⁷³ 1359 H H H H NH — T⁷⁴ 1360 H H H H O — T⁷⁴ 1611361 H H H H NH — T⁷⁵ 1362 H H H H O — T⁷⁵ 1363 H H H H NH — T⁷⁶ 160-1611364 H H H H O — T⁷⁶ 103 1365 H H H H NH — T⁷⁷ 224-225 1366 H H H H O —T⁷⁷ 1367 H H H H NH — T⁷⁸ 1368 H H H H O — T⁷⁸ 1369 H H H H NH — T⁷⁹1370 H H H H O — T⁷⁹ 1371 H H H H NH — T⁸⁰ 1372 H H H H O — T⁸⁰ 104 1373H H H H NH — T⁸¹ 1374 H H H H O — T⁸¹ 1375 H H H H NH — T⁸² 134-136 1376H H H H O — T⁸² 1377 H H H H NH — T⁸³ 158-160 1378 H H H H O — T⁸³ 1379H H H H NH — T⁸⁴ 1380 H H H H O — T⁸⁴ 1381 H H H H NH — T⁸⁵ 1382 H H H HO — T⁸⁵ 1383 H H H H NH — T⁸⁶ 1384 H H H H O — T⁸⁶ 1385 H H H H NH — T⁸⁷123-124 1386 H H H H O — T⁸⁷ 75 1387 H H H H NH — T⁸⁸ 156-157 1388 H H HH O — T⁸⁸ 1389 H H H H NH — T⁸⁹ 1390 H H H H O — T⁸⁹ 65 1391 H H H H NH— T⁹⁰ 1392 H H H H O — T⁹⁰ 1393 H H H H NH — T⁹¹ 1394 H H H H O — T⁹¹1395 H H H H NH — T⁹² 1396 H H H H O — T⁹² 1397 H H H H NH — T⁹³ 1398 HH H H O — T⁹³ 1399 H H H H NH — T⁹⁴ 1400 H H H H O — T⁹⁴ 78-81 1401 H HH H NH — T⁹⁵ 1402 H H H H O — T⁹⁵ 57 1403 H H H H NH — T⁹⁶ 1404 H H H HO — T⁹⁶ 1405 H H H H NH — T⁹⁷ 1406 H H H H O — T⁹⁷ 97 1407 H H H H NH —T⁹⁸ 1408 H H H H O — T⁹⁸ 1409 H H H H NH — T⁹⁹ 1410 H H H H O — T⁹⁹ 1411H H H H NH — T¹⁰⁰ 1412 H H H H O — T¹⁰⁰ 1413 H H H H NH — T¹⁰¹ 1414 H HH H O — T¹⁰¹ 1415 H H H H NH — T¹⁰² 1416 H H H H O — T¹⁰² 1417 H H H HNH — T¹⁰³ 1418 H H H H O — T¹⁰³ 1419 H H H H NH — T¹⁰⁴ 1420 H H H H O —T¹⁰⁴ 107 1421 H H H H NH — T¹⁰⁵ 1422 H H H H O — T¹⁰⁵ 1423 H H H H NH —T¹⁰⁶ 1424 H H H H O — T¹⁰⁶ 1425 H H H H NH — T¹⁰⁷ 1426 H H H H O — T¹⁰⁷oil 1427 H H H H NH — T¹⁰⁸ 1428 H H H H O — T¹⁰⁸ 1429 H H H H NH — T¹⁰⁹1430 H H H H O — T¹⁰⁹ 1431 H H H H NH — T¹¹⁰ 1432 H H H H O — T¹¹⁰ 1433H H H H NH — T¹¹¹ 1434 H H H H O — T¹¹¹ oil 1435 H H H H NH — T¹¹² 1436H H H H O — T¹¹² oil 1437 H H H H NH — T¹¹³ 1438 H H H H O — T¹¹³ 1439 HH H H NH — T¹¹⁴ 1440 H H H H O — T¹¹⁴ 1441 H H H H NH — T¹¹⁵ 1442 H H HH O — T¹¹⁵ oil 1443 H H H H NH — T¹¹⁶ 1444 H H H H O — T¹¹⁶ 1445 H H H HNH — T¹¹⁷ 1446 H H H H O — T¹¹⁷ 1447 H H H H NH — T¹¹⁸ 1448 H H H H O —T¹¹⁸ oil 1449 H H H H NH — T¹¹⁹ 1450 H H H H O — T¹¹⁹ 1451 H H H H NH —T¹²⁰ 1452 H H H H O — T¹²⁰ 1453 H H H H NH — T¹²¹ 1454 H H H H O — T¹²¹1455 H H H H NH — T¹²² 1456 H H H H O — T¹²² oil 1457 H H H H NH — T¹²³1458 H H H H O — T¹²³ 80 1459 H H H H NH — T¹²⁴ 1460 H H H H O — T¹²⁴1461 H H H H NH — T¹²⁵ 1462 H H H H O — T¹²⁵ 1463 H H H H NH — T¹²⁶ 1464H H H H O — T¹²⁶ 1465 H H H H NH — T¹²⁷ 1466 H H H H O — T¹²⁷ 1467 H H HH NH — T¹²⁸ 1468 H H H H O — T¹²⁸ 1469 H H H H NH — T¹²⁹ 1470 H H H H O— T¹²⁹ 1471 H H H H NH — T¹³⁰ 1472 H H H H O — T¹³⁰ 1473 H H H H NH —T¹³¹ 1474 H H H H O — T¹³¹ 1475 H H H H NH — T¹³² 1476 H H H H O — T¹³²1477 H H H H NH — T¹³³ 1478 H H H H O — T¹³³ 1479 H H H H NH — T¹³⁴ 1480H H H H O — T¹³⁴ 1481 H H H H NH — T¹³⁵ 1482 H H H H O — T¹³⁵ 1483 H H HH NH — T¹³⁶ 1484 H H H H O — T¹³⁶ 1485 H H H H NH — T¹³⁷ 1486 H H H H O— T¹³⁷ 1487 H H H H NH — T¹³⁸ 1488 H H H H O — T¹³⁸ 1489 H H H H NH —T¹³⁹ 1490 H H H H O — T¹³⁹ 1491 H H H H NH — T¹⁴⁰ 1492 H H H H O — T¹⁴⁰1493 H H H H NH — T¹⁴¹ 1494 H H H H O — T¹⁴¹ 1495 H H H H NH — T¹⁴² 1496H H H H O — T¹⁴² 1497 H H H H NH — T¹⁴³ 1498 H H H H O — T¹⁴³ 1499 H H HH NH — T¹⁴⁴ 1500 H H H H O — T¹⁴⁴ 1501 H H H H NH — T¹⁴⁵ 1502 H H H H O— T¹⁴⁵ 1503 H H H H NH — T¹⁴⁶ 1504 H H H H O — T¹⁴⁶ 1505 H H H H NH —T¹⁴⁷ 1506 H H H H O — T¹⁴⁷ 1507 H H H H NH — T¹⁴⁸ 1508 H H H H O — T¹⁴⁸1509 H H H H NH — T¹⁴⁹ 1510 H H H H O — T¹⁴⁹ 1511 H H H H NH — T¹⁵⁰ 1512H H H H O — T¹⁵⁰ 1513 H H H H NH — T¹⁵¹ 188-189 1514 H H H H O — T¹⁵¹118 1515 H H H H NH — T¹⁵² 1516 H H H H O — T¹⁵² 1517 H H H H NH — T¹⁵³1518 H H H H O — T¹⁵³ 1519 H H H H NH — T¹⁵⁴ 1520 H H H H O — T¹⁵⁴ 1521H H H H NH — T¹⁵⁵ 1522 H H H H O — T¹⁵⁵ 1523 H H H H NH — T¹⁵⁶ 1524 H HH H O — T¹⁵⁶ 1525 H H H H NH — T¹⁵⁷ 1526 H H H H O — T¹⁵⁷ 1527 H H H HNH — T¹⁵⁸ 1528 H H H H O — T¹⁵⁸ 1529 H H H H NH — T¹⁵⁹ 1530 H H H H O —T¹⁵⁹ 1531 H H H H NH — T¹⁶⁰ 78-80 1532 H H H H O — T¹⁶⁰ 1533 H H H H NH— T¹⁶¹ 92-94 1534 H H H H O — T¹⁶¹ 1535 H H H H NH — T¹⁶² 1536 H H H H O— T¹⁶² 1537 H H H H NH — T¹⁶³ 1538 H H H H O — T¹⁶³ 1539 H H H H NH —T¹⁶⁴ 1540 H H H H O — T¹⁶⁴ 1541 H H H H NH — T¹⁶⁵ 1542 H H H H O — T¹⁶⁵1543 H H H H NH — T¹⁶⁶ 1544 H H H H O — T¹⁶⁶ 1545 H H H H NH — T¹⁶⁷ 1546H H H H O — T¹⁶⁷ 1547 H H H H NH — T¹⁶⁸ 1548 H H H H O — T¹⁶⁸ 1549 H H HH NH — T¹⁶⁹ 1550 H H H H O — T¹⁶⁹ 1551 H H H H NH — T¹⁷⁰ 1552 H H H H O— T¹⁷⁰ 1553 H H H H NH — T¹⁷¹ 1554 H H H H O — T¹⁷¹ 1555 H H H H NH —T¹⁷² 1556 H H H H O — T¹⁷² 1557 H H H H NH — T¹⁷³ 1558 H H H H O — T¹⁷³1559 H H H H NH — T¹⁷⁴ 1560 H H H H O — T¹⁷⁴ 1561 H H H H NH — T¹⁷⁵ 1562H H H H O — T¹⁷⁵ 1563 H H H H NH — T¹⁷⁶ 1564 H H H H O — T¹⁷⁶ 1565 H H HH NH — T¹⁷⁷ 1566 H H H H O — T¹⁷⁷ 1567 H H H H NH — T¹⁷⁸ 1568 H H H H O— T¹⁷⁸ 1569 H H H H NH — T¹⁷⁹ 1570 H H H H O — T¹⁷⁹ 1571 H H H H NH —T¹⁸⁰ 1572 H H H H O — T¹⁸⁰ 1573 H H H H NH — T¹⁸¹ 1574 H H H H O — T¹⁸¹1575 H H H H NH — T¹⁸² 1576 H H H H O — T¹⁸² 1577 H H H H NH — T¹⁸³ 1578H H H H O — T¹⁸³ 1579 H H H H NH — T¹⁸⁴ 1580 H H H H O — T¹⁸⁴ 1581 H H HH NH — T¹⁸⁵ 1582 H H H H O — T¹⁸⁵ 1583 H H H H NH — T¹⁸⁶ 1584 H H H H O— T¹⁸⁶ 1585 H H H H NH — T¹⁸⁷ 1586 H H H H O — T¹⁸⁷ 1587 H H H H NH —T¹⁸⁸ 1588 H H H H O — T¹⁸⁸ 1589 H H H H NH — T¹⁸⁹ 1590 H H H H O — T¹⁸⁹1591 H H H H NH — T¹⁹⁰ 1592 H H H H O — T¹⁹⁰ 1593 H H H H NH — T¹⁹¹ 1594H H H H O — T¹⁹¹ 1595 H H H H NH — T¹⁹² 1596 H H H H O — T¹⁹² 1597 H H HH NH — T¹⁹³ 1598 H H H H O — T¹⁹³ 1599 H H H H NH — T¹⁹⁴ 1600 H H H H O— T¹⁹⁴ 1601 H H H H NH — T¹⁹⁵ 1602 H H H H O — T¹⁹⁵ 1603 H H H H NH —T¹⁹⁶ 1604 H H H H O — T¹⁹⁶ 1605 H H H H NH — T¹⁹⁷ 1606 H H H H O — T¹⁹⁷1607 H H H H NH — T¹⁹⁸ 1608 H H H H O — T¹⁹⁸ 1609 H H H H NH — T¹⁹⁹ 1610H H H H O — T¹⁹⁹ 1611 H H H H NH — T²⁰⁰ 1612 H H H H O — T²⁰⁰ 1613 H H HH NH — T²⁰¹ 1614 H H H H O — T²⁰¹ 1615 H H H H NH — T²⁰² 1616 H H H H O— T²⁰² 1617 H H H H NH — T²⁰³ 1618 H H H H O — T²⁰³ 1619 H H H H NH —T²⁰⁴ 1620 H H H H O — T²⁰⁴ 1621 H H H H NH — T²⁰⁵ 1622 H H H H O — T²⁰⁵1623 H H H H NH — T²⁰⁶ 1624 H H H H O — T²⁰⁶ 1625 H H H H NH — T²⁰⁷ 1626H H H H O — T²⁰⁷ 1627 H H H H NH — T²⁰⁸ 1628 H H H H O — T²⁰⁸ 1629 H H HH NH — T²⁰⁹ 1630 H H H H O — T²⁰⁹ 1631 H H H H NH — T²¹⁰ 1632 H H H H O— T²¹⁰ 1633 H H H H NH — T²¹¹ 1634 H H H H O — T²¹¹ 1635 H H H H NH —T²¹² 1636 H H H H O — T²¹² 1637 H H H H NH — T²¹³ 1638 H H H H O — T²¹³1639 H H H H NH — T²¹⁴ 1640 H H H H O — T²¹⁴ 1641 H H H H NH — T²¹⁵ 1642H H H H O — T²¹⁵ 1643 H H H H NH — T²¹⁶ 1644 H H H H O — T²¹⁶ 1645 H H HH NH — T²¹⁷ 1646 H H H H O — T²¹⁷ 1647 H H H H NH — T²¹⁸ 1648 H H H H O— T²¹⁸ 1649 H H H H NH — T²¹⁹ 1650 H H H H O — T²¹⁹ 1651 H H H H NH —T²²⁰ 1652 H H H H O — T²²⁰ 1653 H H H H NH — T²²¹ 1654 H H H H O — T²²¹1655 H H H H NH — T²²² 1656 H H H H O — T²²² 1657 H H H H NH — T²²³ 1658H H H H O — T²²³ 1659 H H H H NH — T²²⁴ 1660 H H H H O — T²²⁴ 1661 H H HH NH — T²²⁵ 1662 H H H H O — T²²⁵ 1663 H H H H NH — T²²⁶ 1664 H H H H O— T²²⁶ 1665 H H H H NH — T²²⁷ 1666 H H H H O — T²²⁷ 1667 H H H H NH —T²²⁸ 1668 H H H H O — T²²⁸ 1669 H H H H NH — T²²⁹ 1670 H H H H O — T²²⁹1671 H H H H NH — T²³⁰ 1672 H H H H O — T²³⁰ 1673 H H H H NH — T²³¹ 1674H H H H O — T²³¹ 1675 H H H H NH — T²³² 1676 H H H H O — T²³² 1677 H H HH NH — T²³³ 1678 H H H H O — T²³³ 1679 H H H H NH — T²³⁴ 1680 H H H H O— T²³⁴ 1681 H H H H NH — T²³⁵ 1682 H H H H O — T²³⁵ 1683 H H H H NH —T²³⁶ 1684 H H H H O — T²³⁶ 1685 H H H H NH — T²³⁷ 1686 H H H H O — T²³⁷1687 H H H H NH — T²³⁸ 1688 H H H H O — T²³⁸ 1689 H H H H NH — T²³⁹ 1690H H H H O — T²³⁹ 1691 H H H H NH — T²⁴⁰ 1692 H H H H O — T²⁴⁰ 1693 H H HH NH — T²⁴¹ 1694 H H H H O — T²⁴¹ 1695 H H H H NH — T²⁴² 1696 H H H H O— T²⁴² 1697 H H H H NH — T²⁴³ 1698 H H H H O — T²⁴³ 1699 H H H H NH —T²⁴⁴ 1700 H H H H O — T²⁴⁴ 1701 H H H H NH — T²⁴⁵ 1702 H H H H O — T²⁴⁵1703 H H H H NH — T²⁴⁶ 1704 H H H H O — T²⁴⁶ 1705 H H H H NH — T²⁴⁷ 1706H H H H O — T²⁴⁷ 1707 H H H H NH — T²⁴⁸ 1708 H H H H O — T²⁴⁸

TABLE III

Example No. A B X E Q M.p. [° C.] 1709 CH S NH — T⁷ 1710 ″ ″ O — T⁷ 1711S CH NH — T⁷ 1712 ″ ″ O — T⁷ 1713 CH S NH — T⁹ 1714 S CH O — T⁹ 1715 SCH NH — T⁹ 1716 ″ ″ O — T⁹ 1717 CH S NH — T⁸ 1718 ″ ″ O — T⁸ 1719 S CHNH — T⁸ 1720 ″ ″ O — T⁸ 1721 CH S NH — T⁴ 1722 ″ ″ O — T⁴ 1723 S CH NH —T⁴ 1724 ″ ″ O — T⁴ 1725 CH S NH — T¹⁰ 1726 ″ ″ O — T¹⁰ 1727 S CH NH —T¹⁰ 1728 S CH O — T¹⁰ 1729 CH S NH — T¹¹ 1730 ″ ″ O — T¹¹ 1731 S CH NH —T¹¹ 1732 ″ ″ O — T¹¹ 1733 CH S NH — T¹² 1734 ″ ″ O — T¹² 1735 S CH NH —T¹² 1736 ″ ″ O — T¹² 1737 CH S NH — T¹⁴ 1738 ″ ″ O — T¹⁴ 1739 S CH NH —T¹⁴ 1740 ″ ″ ″ — T¹⁴ 1741 CH S NH T²³ 118-120 1742 ″ ″ O — T²³ 1743 S CHNH — T²³ 1744 ″ ″ O — T²³ 1745 CH S NH T⁵⁸ 1746 ″ ″ O T⁵⁸ 1747 S CH NHT⁵⁸ 1748 ″ ″ O T⁵⁸

TABLE IV

Example No. X R M.p. [° C.] 1749 NH

238-240 1750 NH

152-154

TABLE V

Example No. X M.p. [° C.] 1751 NH T⁴ 1752 NH T⁷ 1753 NH T⁸ 1754 NH T⁹1755 O T⁹ 1756 NH T¹⁰ 1757 NH T¹² 1758 NH T¹⁴ 1759 NH T²³ 1760 O T²³1761 NH T⁶⁶ 1762 NH T⁶⁸ 1763 NH T⁷⁰ 1764 O T⁷⁰ 1765 NH T⁷⁶ 1766 O T⁷⁶

TABLE VI

Example No. X M.p. [° C.] 1767 NH T⁴ 1768 NH T⁷ 1769 NH T⁸ 1770 NH T⁹1771 O T⁹ 1772 NH T¹⁰ 1773 NH T¹² 1774 NH T¹⁴ 1775 NH T²³ 1776 O T²³1777 NH T⁶⁶ 1778 NH T⁶⁸ 1779 NH T²⁰ 1780 O T²⁰ 1781 NH T⁷⁶ 1782 O T⁷⁶

TABLE VII

Example No. X M.p. [° C.] 1783 NH T⁴ 1784 NH T⁷ 1785 NH T⁸ 1786 NH T⁹1787 O T⁹ 1788 NH T¹⁰ 1789 NH T¹² 1790 NH T¹⁴ 1791 NH T²³ 1792 O T²³1793 NH T⁶⁶ 1794 NH T⁶⁸ 1795 NH T⁷⁰ 1796 O T⁷⁰ 1797 NH T⁷⁶ 1798 O T⁷⁶

TABLE VIII

Example No. X M.p. [°C.] 1799 NH T⁴ 1800 NH T⁷ 1801 NH T⁸ 1802 NH T⁹1803 O T⁹ 1804 NH T¹⁰ 1805 NH T¹² 1806 NH T¹⁴ 1807 NH T²³ 1808 O T²³1809 NH T⁶⁶ 1810 NH T⁶⁸ 1811 NH T⁷⁰ 1812 O T⁷⁰ 1813 NH T⁷⁶ 1814 O T⁷⁶

What is claimed is:
 1. A compound of the formula I

in which R¹ is hydrogen, halogen, (C_(1-C) ₄)-alkyl or(C₃-C₆)-cycloalkyl, R² is hydrogen, (C₁-C₄)-alkyl, halogen,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylthio-(₁-C₄)-alkyl, (C₁-C₄)-alkyl-amino ordi-(C₁-C₄)-alkylamino, R³ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, halogen, (C₁-C₄)-alkylthio, amino,(C₁-C₄)-alkylamino or di-(C₁-C₄)-alkyl-amino or R² and R³ together withthe carbon atoms to which they are bonded form an unsaturated 5- or6-membered carbocyclic ring which, if it is a 5-membered ring, cancontain an oxygen or sulfur atom in place of CH₂ and which is optionallysubstituted by 1, 2 or 3 identical or different radicals, these radicalsbeing (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy or halogen, or R² and R³ together with the carbonatoms to which they are bonded form a saturated 5- 6- or 7-memberedcarbocyclic ring which can contain an oxygen or sulfur atom in place ofCH₂ and which is optionally substituted by 1, 2 or 3 (CH₁-C₄)-alkylgroups, X is NH or oxygen, E is a direct bond or a straight-chain orbranched (C₁-C₄)-alkanediyl group, Q has the meaning Q¹ and Q¹ is acycloalkyl group of the formula II

in which n is an integer from 2 to 7, R⁴ and R⁵ are identical ordifferent and are in each case hydrogen, (C₁-C₁₂)-alkyl,(C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl,(C₁-C₈)-alkoxy,(C₃-C₈)-cycloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, tri-(C₁-C₈)-alkylsilyl,di-(C₁-C₈)-alkyl-(C₃-C₈)-cycloalkyl-silyl,di-(C₁-C₈)-alkyl-(phenyl-(C₁-C₄)-alkyl)-silyl,di-(C₁-C₈)-alkyl-(C₁-C₄)-haloalkylsilyl, dimethylphenyl silyl,(C₁-C₄)-haloalkyl, halogen, (C₁-C₄)-haloalkoxy, heteroaryl, phenyl,phenyl-(C₁-C₄)-alkyl, benzyloxy, benzyloxy-(C₁-C₄)-alkyl, benzylthio,phenylthio or phenoxy, it being possible for the phenyl rings in theseven last-mentioned radicals to be unsubstituted or provided with oneor two substituents and these substituents are identical or differentand can be in each case (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl,(C₁-C₄)-haloalkyl, halogen, (C₁-C₄)-dialkylamino, (C₁-C₄)-alkylthio,(C₁-C₈)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,H₅C₂—O—[CH₂-CH₂-O]_(y),2-(tetrahydro-2H-pyran-2-yloxy)-ethoxy,(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, benzyloxy which in the phenyl radicaloptionally carries one or two identical or different substituentsselected from the group comprising (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and halogen, ortri-(C₁-C₄)-alkylsilylmethoxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy,1,3-dioxolan-2-ylmethoxy, tetrahydrofuran-2-ylmethoxy ortetrahydro-2H-pyran-2-ylmethoxy, and at least one of R⁴ and R⁵ isheteroaryl, wherein the term heteroaryl is aryl in which at least one CHgroup is replace by N and/or at least two adjacent CH groups arereplaced by S, NH or O, and wherein aryl is phenyl, naphtyl or biphenyl,y is 2, 3 or 4, or Q has the meaning Q² and Q² is a group of the formulaIII

in which R⁶ is a group of the formula Z-W and Z is a direct bond orcarbonyl or sulfonyl and W is optionally substituted heteroaryl, whichheteroaryl is as defined above for R⁴ and R⁵ with the exception ofheteroaryl selected from the group consisting 2-pyridyl, 2-quinoxalinyland 2-pyrimidinyl, and which heteroaryl can be unsubstituted or providedwith one or two substituents and these substituents are identical ordifferent and are in each case (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl,trifluoromethyl, halogen, (C₁-C₄)-alkoxy, (C₁-C₈)-dialkylamino or(C₁-C₄)-alkythio, or acid addition salts thereof.
 2. A compound of theformula I as claimed in claim 1, in which R¹ is hydrogen, methyl orcyclopropyl, R² is (C₁-C₄)-alkyl, chlorine, methoxy, ethoxy ormethoxymethyl, R³ is hydrogen, (C₁-C₃)-alkyl, methoxy, ethoxy or halogenor R² and R³ together with the carbon atoms to which they are bondedform an unsaturated 5- or 6-membered ring which can contain an oxygen orsulfur atom, or R² and R³ together with the carbon atoms to which theyare bonded form a saturated 5- or 6-membered ring which can contain asulfur atom, Q has the meaning Q¹ or Q², or acid addition salts thereof.3. A compound of the formula I as claimed in claim 1, in which R¹ ishydrogen or methyl, R² is methyl, ethyl, methoxy, ethoxy, ormethoxy-methyl, R³ is methyl, ethyl, methoxy, chlorine or bromine, or R²and R³ together with the carbon atoms to which they are bonded form thequinazoline system, which can be mono-, di- or trisubstituted byfluorine, chlorine, bromine, methyl and/or methoxy, or R² and R³together with the carbon atoms to which they are bonded form a saturated6-membered ring which can contain a sulfur atom and Q has the meaning Q¹and Q², or acid addition salts thereof.
 4. A compound of the formula Ias claimed in claim 1, in which E is a direct bond, R¹ is hydrogen, R²is methyl, ethyl or methoxymethyl, R³ is chlorine, bromine, or methoxyor R² and R³ together with the carbon atoms to which they are bondedform the quinazoline system which can be substituted by fluorine,chlorine, bromine or methyl, or R² and R³ together with the pyridimidinering form the 5,6,7,8-tetrahydroquinazoline system or the5,6-dihydro-7H-thiopyrano[2,3-d] pyrimidine or the5,6-dihydro-8H-thiopyrano[3,4-d] pyrimidine system and Q has the meaningQ¹ or Q₂, or acid addition salts thereof.
 5. A compound of the formula Ias claimed in claim 1, in which R¹ is hydrogen, R² is methoxymethyl andR³ is methoxy or R² is methyl or ethyl and R³ is chlorine or bromine orR² and R³ together with the carbon atom to which they are bonded form aquinazoline system which is substituted by fluorine, chlorine, ormethyl, or form a 5,6,7,8-tetrahydro-quinazolin system and Q has themeaning Q¹, or acid addition salts thereof.
 6. A compound of the formulaI as claimed in claim 1, in which E is a direct bond, R¹ is hydrogen, R²is methoxymethyl and R³ is methoxy or R² is ethyl and R³ is chlorine orR² and R³ together with the carbon atom to which they are bonded form aquinazoline or a 5,6,7,8-tetrahydroquinazoline system and Q¹ is acycloalkyl group of the formula II which is substituted in the 3- or4-position and in which n is 4 or 5, R⁴ is (C₃-C₈)-alkyl, cyclopentyl,cyclohexyl, phenyl or phenoxy, it being possible for the twolast-mentioned radicals to be unsubstituted or provided with one or twosubstituents which can be identical or different and which are fluorine,chlorine, bromine, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, trifluoromethyl,(C₁-C₂)-haloalkoxy, cyclohexyl, 2-ethoxyethoxy, methylthio ordimethylamino, or acid addition salts thereof.
 7. A compound of theformula I as claimed in claim 1, in which E is a direct bond, R¹ ishydrogen, R² is methoxymethyl and R³ is methoxy or R² is ethyl and R³ ischlorine, or R² and R³ together with the carbon atoms to which they arebonded form a quinazoline or a 5,6,7,8-tetrahydroquinazoline system, Qhas the meaning Q¹ and Q¹ is cyclohexyl which is substituted in the4-position, and E and the substituent in the 4-position of thecyclohexyl are in the cis-position relative to each other, or acidaddition salts thereof.
 8. An insecticidal or acaricidal compositionwhich comprises an effective amount of a compound of the formula I asclaimed in claim 1 and suitable formulation auxiliaries.
 9. A method ofcontrolling insect pests and acarids, which comprises applying aneffective amount of a compound of the formula I as claimed in claim 1 tothese insect pests or acarids or to the plants, areas or substrateswhich are infested with them.